Safened herbicidal compositions comprising pyridine carboxylic acids

ABSTRACT

Disclosed herein are safened herbicidal compositions comprising (a) a pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) an azole carboxylate safener, or agriculturally acceptable salt or ester thereof. Also disclosed herein are methods of controlling undesirable vegetation, comprising applying to vegetation or an area adjacent the vegetation or applying in soil or water to control the emergence or growth of vegetation (a) a pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) an azole carboxylate safener, or agriculturally acceptable salt or ester thereof.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims benefit of U.S. Provisional Patent ApplicationNo. 62/050,697, filed Sep. 15, 2014, and U.S. Provisional PatentApplication No. 62/050,702, filed Sep. 15, 2014, which are herebyincorporated herein by reference in their entireties.

FIELD OF THE DISCLOSURE

The disclosure relates to safened herbicidal compositions comprising apyridine carboxylic acid herbicide, as well as methods of controllingundesirable vegetation using the same.

BACKGROUND

Many recurring problems in agriculture involve controlling the growth ofundesirable vegetation that can, for instance, negatively affect thegrowth of desirable vegetation. To help control undesirable vegetation,researchers have produced a variety of chemicals and chemicalformulations effective in controlling such unwanted growth.

In some cases, although a herbicide may be effective in controllingundesirable vegetation, it may also have a phytotoxic effect on a cropand cause injury or even kill the crop. Accordingly, safeners can beprovided with the herbicide to limit the phytotoxicity of the herbicidalactive ingredient.

SUMMARY OF THE DISCLOSURE

Disclosed herein are safened herbicidal compositions. The safenedherbicidal compositions can comprise (a) a pyridine carboxylic acidherbicide or agriculturally acceptable N-oxide, salt, or ester thereof;and (b) an azole carboxylate safener, or an agriculturally acceptablesalt or ester thereof. The weight ratio of (a) in grams acid equivalentper hectare (g ae/ha) to (b) in grams active ingredient per hectare (gai/ha) can be from 65:1 to 1:5 (e.g., from 5:1 to 1:5, or from 2:1 to1:2).

The pyridine carboxylic acid herbicide can comprise a compound definedby Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″), wherein R^(1′) is hydrogen, C₁-C₈ alkyl,or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is one of groups A1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″), if applicable to the A group, are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₁-C₄haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (II):

wherein

R¹ is OR^(1′) or NR^(1″)R^(1″), wherein R^(1′) is hydrogen, C₁-C₈ alkyl,or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl. In certain embodiments, R² is Cl, methoxy,vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; A is A15; R⁵ is hydrogenor F; R⁶ is hydrogen or F; and R^(6″) is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (III):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″), wherein R^(1′) is hydrogen, C₁-C₈ alkyl,or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, X is N, CH or CF. In certain embodiments, X is CF,R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀arylalkyl; R² is Cl, methoxy, vinyl, or 1-propenyl; R³ and R⁴ arehydrogen; R⁶ is hydrogen or F; and R^(6′) is hydrogen, halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide caninclude 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinicacid, or an agriculturally acceptable N-oxide, salt, or ester thereof.

In some embodiments, the azole carboxylate safener can be selected fromthe group consisting of fenchlorazole, isoxadifen, mefenpyr,agriculturally acceptable salts or esters thereof, and combinationsthereof.

In some embodiments, the composition can further comprise anagriculturally acceptable adjuvant or carrier, an additional pesticide,or a combination thereof. In certain embodiments, the active ingredientsin the composition consist of (a) and (b).

Also disclosed herein are methods of controlling undesirable vegetation,comprising applying to vegetation or an area adjacent the vegetation orapplying to soil or water to control the emergence or growth ofvegetation (a) a pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof and (b) an azole carboxylatesafener or an agriculturally acceptable salt or ester thereof. In someembodiments, (a) and (b) are applied simultaneously. In someembodiments, (a) and (b) are applied post-emergence of the undesirablevegetation. In some embodiments, the undesirable vegetation can becontrolled in a crop (e.g., in wheat, corn/maize, barley, tame oats,rice, or a combination thereof). In some embodiments, the undesirablevegetation can be controlled in wheat. In some embodiments, theundesirable vegetation can be controlled in corn (e.g., maize).

In some embodiments, (a) can comprise a pyridine carboxylic acidherbicide described above. In some embodiments, the azole carboxylatesafener can be selected from the group consisting of fenchlorazole,isoxadifen, mefenpyr, agriculturally acceptable salts or esters thereof,and combinations thereof. In some cases, (a) can be applied in an amountof from 0.1 g ae/ha to 300 g ae/ha (e.g., from 30 g ae/ha to 40 g ae/ha)and/or (b) can be applied in an amount of from 1 g ai/ha to 300 g ae/ha(e.g., from 30 g ai/ha to 40 g ai/ha). In some cases, (a) in g ae/ha and(b) in g ai/ha can be applied in a weight ratio of from 65:1 to 1:5(e.g., from 5:1 to 1:5, or from 2:1 to 1:2).

The description below sets forth details of one or more embodiment ofthe present disclosure. Other features, objects, and advantages will beapparent from the description and from the claims.

DETAILED DESCRIPTION

The present disclosure relates to safened herbicidal compositionscomprising a herbicidally effective amount of (a) a pyridine carboxylicacid herbicide, or an agriculturally acceptable N-oxide, salt, or esterthereof, and (b) a azole carboxylate safener. The present disclosurealso relates to methods for controlling undesirable vegetation. In someembodiments, the undesirable vegetation can be controlled in a crop(e.g., in wheat, corn/maize, barley, tame oats, rice, or a combinationthereof). In some embodiments, the undesirable vegetation can becontrolled in wheat. In some embodiments, the undesirable vegetation canbe controlled in corn (e.g., maize).

I. DEFINITIONS

Terms used herein will have their customary meaning in the art unlessspecified otherwise. The organic moieties mentioned when definingvariable positions within the general formulae described herein (e.g.,the term “halogen”) are collective terms for the individual substituentsencompassed by the organic moiety. The prefix C_(n)-C_(m) preceding agroup or moiety indicates, in each case, the possible number of carbonatoms in the group or moiety that follows.

As used herein, the terms “herbicide” and “herbicidal active ingredient”refer to an active ingredient that kills, controls, or otherwiseadversely modifies the growth of vegetation, particularly undesirablevegetation, such as weeds, when applied in an appropriate amount.

As used herein, a herbicidally effective amount” refers to an amount ofan active ingredient that causes a “herbicidal effect,” i.e., anadversely modifying effect including, for instance, a deviation fromnatural growth or development, killing, regulation, desiccation, growthinhibition, growth reduction, and retardation.

As used herein, applying a herbicide or herbicidal composition refers todelivering it directly to the targeted vegetation or to the locusthereof or to the area where control of undesired vegetation is desired.Methods of application include, but are not limited to pre-emergentlycontacting soil or water, post-emergently contacting the undesirablevegetation or area adjacent to the undesirable vegetation.

As used herein, the terms “crops” and “vegetation” can include, forinstance, dormant seeds, germinant seeds, emerging seedlings, plantsemerging from vegetative propagules, immature vegetation, andestablished vegetation.

As used herein, immature vegetation refers to small vegetative plantsprior to reproductive stage, and mature vegetation refers to vegetativeplants during and after the reproductive stage.

As used herein, the term “acyl” refers to a group of formula —C(O)R,where R is hydrogen, alkyl (e.g., C₁-C₁₀ alkyl), haloalkyl (C₁-C₈haloalkyl), alkenyl (C₂-C₈ alkenyl), haloalkenyl (e.g., C₂-C₈haloalkenyl), alkynyl (e.g., C₂-C₈ alkynyl), alkoxy (C₁-C₈ alkoxy),haloalkoxy (C₁-C₈ alkoxy), aryl, or heteroaryl, arylalkyl (C₇-C₁₀arylalkyl), as defined below, where “C(O)” or “CO” is short-handnotation for C═O. In some embodiments, the acyl group can be a C₁-C₆acyl group (e.g., a formyl group, a C₁-C₅ alkylcarbonyl group, or aC₁-C₅ haloalkylcarbonyl group). In some embodiments, the acyl group canbe a C₁-C₃ acyl group (e.g., a formyl group, a C₁-C₃ alkylcarbonylgroup, or a C₁-C₃ haloalkylcarbonyl group).

As used herein, the term “alkyl” refers to saturated, straight-chainedor branched saturated hydrocarbon moieties. Unless otherwise specified,C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl groups areintended. Examples of alkyl groups include methyl, ethyl, propyl,1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl-propyl,1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl,3-methyl-butyl, 2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl,1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl-pentyl,2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl,1,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl,2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl,1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1-ethyl-1-methyl-propyl,and 1-ethyl-2-methyl-propyl. Alkyl substituents may be unsubstituted orsubstituted with one or more chemical moieties. Examples of suitablesubstituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl,hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl,aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided thatthe substituents are sterically compatible and the rules of chemicalbonding and strain energy are satisfied. Preferred substituents includecyano and C₁-C₆ alkoxy.

As used herein, the term “haloalkyl” refers to straight-chained orbranched alkyl groups, wherein these groups the hydrogen atoms maypartially or entirely be substituted with halogen atoms. Unlessotherwise specified, C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄)alkyl groups are intended. Examples include chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, and1,1,1-trifluoroprop-2-yl. Haloalkyl substituents may be unsubstituted orsubstituted with one or more chemical moieties. Examples of suitablesubstituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl,hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl,aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided thatthe substituents are sterically compatible and the rules of chemicalbonding and strain energy are satisfied. Preferred substituents includecyano and C₁-C₆ alkoxy.

As used herein, the term “alkenyl” refers to unsaturated,straight-chained, or branched hydrocarbon moieties containing a doublebond. Unless otherwise specified, C₂-C₂₀ (e.g., C₂-C₁₂, C₂-C₁₀, C₂-C₈,C₂-C₆, C₂-C₄) alkenyl groups are intended. Alkenyl groups may containmore than one unsaturated bond. Examples include ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl. The term“vinyl” refers to a group having the structure —CH═CH₂; 1-propenylrefers to a group with the structure —CH═CH—CH₃; and 2-propenyl refersto a group with the structure —CH₂—CH═CH₂. Alkenyl substituents may beunsubstituted or substituted with one or more chemical moieties.Examples of suitable substituents include, for example, hydroxy, nitro,cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl,haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆dihaloalkylaminocarbonyl, provided that the substituents are stericallycompatible and the rules of chemical bonding and strain energy aresatisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

The term “haloalkenyl,” as used herein, refers to an alkenyl group, asdefined above, which is substituted by one or more halogen atoms.

As used herein, the term “alkynyl” represents straight-chained orbranched hydrocarbon moieties containing a triple bond. Unless otherwisespecified, C₂-C₂₀ (e.g., C₂-C₁₂, C₂-C₁₀, C₂-C₈, C₂-C₆, C₂-C₄) alkynylgroups are intended. Alkynyl groups may contain more than oneunsaturated bond. Examples include C₂-C₆-alkynyl, such as ethynyl,1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl,4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.Alkynyl substituents may be unsubstituted or substituted with one ormore chemical moieties. Examples of suitable substituents include, forexample, hydroxy, nitro, cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl,C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl,haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆dihaloalkylaminocarbonyl, provided that the substituents are stericallycompatible and the rules of chemical bonding and strain energy aresatisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

As used herein, the term “alkoxy” refers to a group of the formula R—O—,where R is unsubstituted or substituted alkyl as defined above. Unlessotherwise specified, alkoxy groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂,C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended. Examples includemethoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methyl-propoxy,2-methyl-propoxy, 1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy,2-methyl-butoxy, 3-methyl-butoxy, 2,2-dimethyl-propoxy, 1-ethyl-propoxy,hexoxy, 1,1-dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy,2-methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-penoxy,1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy,2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy,1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy,1,2,2-trimethyl-propoxy, 1-ethyl-1-methyl-propoxy, and1-ethyl-2-methyl-propoxy.

As used herein, the term “haloalkoxy” refers to a group of the formulaR—O—, where R is unsubstituted or substituted haloalkyl as definedabove. Unless otherwise specified, haloalkoxy groups wherein R is aC₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) haloalkyl group areintended. Examples include chloromethoxy, bromomethoxy, dichloromethoxy,trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.

As used herein, the term “alkylthio” refers to a group of the formulaR—S—, where R is unsubstituted or substituted alkyl as defined above.Unless otherwise specified, alkylthio groups wherein R is a C₁-C₂₀(e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended.Examples include methylthio, ethylthio, propylthio, 1-methylethylthio,butylthio, 1-methylpropylthio, 2-methylpropylthio,1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio,3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethyl-propylthio, 1-ethyl-1-methylpropylthio, and1-ethyl-2-methylpropylthio.

As used herein, the term “haloalkylthio” refers to an alkylthio group asdefined above wherein the carbon atoms are partially or entirelysubstituted with halogen atoms. Unless otherwise specified,haloalkylthio groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈,C₁-C₆, C₁-C₄) alkyl group are intended. Examples includechloromethylthio, bromomethylthio, dichloromethylthio,trichloromethylthio, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio,chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio,1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,2,2,2-trichloroethylthio, pentafluoroethylthio, and1,1,1-trifluoroprop-2-ylthio.

As used herein, the term “aryl,” as well as derivative terms such asaryloxy, refers to groups that include a monovalent aromatic carbocyclicgroup of from 6 to 14 carbon atoms. Aryl groups can include a singlering or multiple condensed rings. In some embodiments, aryl groupsinclude C₆-C₁₀ aryl groups. Examples of aryl groups include, but are notlimited to, phenyl, biphenyl, naphthyl, tetrahydronaphthyl,phenylcyclopropyl, and indanyl. In some embodiments, the aryl group canbe a phenyl, indanyl or naphthyl group. The term “heteroaryl”, as wellas derivative terms such as “heteroaryloxy”, refers to a 5- or6-membered aromatic ring containing one or more heteroatoms, viz., N, Oor S; these heteroaromatic rings may be fused to other aromatic systems.The aryl or heteroaryl substituents may be unsubstituted or substitutedwith one or more chemical moieties. Examples of suitable substituentsinclude, for example, hydroxy, halogen, nitro, cyano, formyl, C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl,C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl,C₁-C₆ alkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ carbamoyl,hydroxycarbonyl, C₁-C₆ alkylcarbonyl, aminocarbonyl, C₁-C₆alkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, provided that thesubstituents are sterically compatible and the rules of chemical bondingand strain energy are satisfied. Preferred substituents include halogen,C₁-C₂ alkyl and C₁-C₂ haloalkyl.

As used herein, the term “alkylcarbonyl” refers to an unsubstituted orsubstituted alkyl group bonded to a carbonyl group. C₁-C₃ alkylcarbonyland C₁-C₃ haloalkylcarbonyl refer to groups wherein a C₁-C₃unsubstituted or substituted alkyl or haloalkyl group is bonded to acarbonyl group (the group contains a total of 2 to 4 carbon atoms).

As used herein, the term “alkoxycarbonyl” refers to a group of theformula

wherein R is unsubstituted or substituted alkyl.

As used herein, the term “arylalkyl” refers to an alkyl groupsubstituted with an unsubstituted or substituted aryl group. C₇-C₁₀arylalkyl refers to a group wherein the total number of carbon atoms inthe group is 7 to 10, not including the carbon atoms present in anysubstituents of the aryl group.

As used herein, the term “alkylamino” refers to an amino groupsubstituted with one or two unsubstituted or substituted alkyl groups,which may be the same or different.

As used herein, the term “haloalkylamino” refers to an alkylamino groupwherein the alkyl carbon atoms are partially or entirely substitutedwith halogen atoms.

As used herein, C₁-C₆ alkylaminocarbonyl refers to a group of theformula RNHC(O)— wherein R is C₁-C₆ unsubstituted or substituted alkyl,and C₁-C₆ dialkylaminocarbonyl refers to a group of the formula R₂NC(O)—wherein each R is independently C₁-C₆ unsubstituted or substitutedalkyl.

As used herein, the term “alkylcarbamyl” refers to a carbamyl groupsubstituted on the nitrogen with an unsubstituted or substituted alkylgroup.

As used herein, the term “alkylsulfonyl” refers to a group of theformula

where R is unsubstituted or substituted alkyl.

As used herein, the term “carbamyl” (also referred to as carbamoyl andaminocarbonyl) refers to a group of the formula

As used herein, the term “dialkylphosphonyl” refers to a group of theformula

where R is independently unsubstituted or substituted alkyl in eachoccurrence.

As used herein, C₁-C₆ trialkylsilyl refers to a group of the formula—SiR₃ wherein each R is independently a C₁-C₆ unsubstituted orsubstituted alkyl group (the group contains a total of 3 to 18 carbonatoms).

As used herein, Me refers to a methyl group; OMe refers to a methoxygroup; and i-Pr refers to an isopropyl group.

As used herein, the term “halogen” including derivative terms such as“halo” refers to fluorine, chlorine, bromine and iodine.

As used herein, agriculturally acceptable salts and esters refer tosalts and esters that exhibit herbicidal activity, or that are or can beconverted in plants, water, or soil to the referenced herbicide.Exemplary agriculturally acceptable esters are those that are or can behydrolyzed, oxidized, metabolized, or otherwise converted, e.g., inplants, water, or soil, to the corresponding carboxylic acid which,depending on the pH, may be in the dissociated or undissociated form.

Compounds described herein can include N-oxides. Pyridine N-oxides canbe obtained by oxidation of the corresponding pyridines. Suitableoxidation methods are described, for example, in Houben-Weyl, Methodender organischen Chemie [Methods in organic chemistry], expanded andsubsequent volumes to the 4th edition, volume E 7b, p. 565 f.

Pyridine Carboxylic Acid Herbicides

Compositions and methods of the present disclosure can include apyridine carboxylic acid herbicide defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″) R^(1″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is one of groups A1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″), if applicable to the A group, are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₁-C₄haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl. In some embodiments, R^(1′) is hydrogen orC₁-C₈ alkyl. In some embodiments, R^(1′) is hydrogen.

In some embodiments, R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄alkynyl, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₁-C₄-alkoxy, or C₁-C₄haloalkoxy. In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄haloalkenyl, or C₁-C₄-alkoxy. In some embodiments, R² is halogen. Insome embodiments, R² is C₂-C₄-alkenyl or C₂-C₄ haloalkenyl. In someembodiments, R² is C₁-C₄ alkoxy. In some embodiments, R² is Cl, OMe,vinyl, or 1-propenyl. In some embodiments, R² is Cl. In someembodiments, R² is OMe. In some embodiments, R² is vinyl or 1-propenyl.

In some embodiments, R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆ alkylcarbamyl, or R³ and R⁴ taken togetherrepresent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independentlyhydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy, orC₁-C₆ alkylamino. In some embodiments, R³ and R⁴ are independentlyhydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) andR^(4′) are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy or C₁-C₆alkylamino. In some embodiments, R³ and R⁴ are independently hydrogen,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl,C₁-C₃ alkylcarbonyl, or C₁-C₃ haloalkylcarbonyl. In some embodiments, atleast one of R³ and R⁴ are hydrogen. In some embodiments, R³ and R⁴ areboth hydrogen.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. Insome embodiments, X is CH. In some embodiments, X is CF. In otherembodiments, X is C—CH₃.

In some embodiments, A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11,A12, A13, A14, A15, A16, A17, A18, A19, or A20. In other embodiments, Ais one of A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32,A33, A34, A35, and A36.

In some embodiments, A is one of groups A1, A2, A3, A7, A8, A9, A10,A13, A14, and A15. In some embodiments, A is one of groups A1, A2, A3,A13, A14, and A15. In some embodiments, A is one of groups A13, A14, andA15. In some embodiments, A is A15.

In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, or amino. In some embodiments, R⁵ is hydrogen, halogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, or amino.In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl or C₁-C₄alkoxy. In some embodiments, R⁵ is hydrogen or F. In some embodiments,R⁵ is hydrogen.

In other embodiments, R⁵ is F.

In some embodiments, R⁶ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, or C₁-C₃ haloalkoxy. In some embodiments, R⁶ ishydrogen or fluorine. In some embodiments, R⁶ is hydrogen. In someembodiments, R⁶ is fluorine.

In some embodiments, R^(6′) is hydrogen or halogen. In some embodiments,R^(6′) is hydrogen, F, or Cl. In some embodiments, R^(6′) is hydrogen orF. In some embodiments, R^(6′) is hydrogen.

In some embodiments, R^(6″) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂. In some embodiments,R^(6″) is hydrogen. In some embodiments, R^(6″) is halogen. In someembodiments, R^(6″) is C₁-C₄ alkyl. In some embodiments, R^(6″) is C₁-C₄haloalkyl. In some embodiments, R^(6″) is cyclopropyl. In someembodiments, R^(6″) is C₂-C₄ alkynyl. In some embodiments, R^(6″) is CN.In some embodiments, R^(6″) is NO₂.

In some embodiments:

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl;

R² is chlorine;

R³ and R⁴ are hydrogen;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, OH, amino, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃alkylamino, or cyclopropyl;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, OH, NH₂, CN,C₁-C₃ alkyl, C₁-C₃ alkoxy, cyclopropyl, or vinyl;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃alkoxy, C₁-C₃ alkylthio, cyclopropyl, C₁-C₃ alkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₃ alkyl, phenyl, or C₁-C₃ alkylcarbonyl.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄ alkoxy; R³ and R⁴ are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is halogen; R³ and R⁴ are both hydrogen; and Xis N, CH, or CF.

In some embodiments, R² is C₂-C₄-alkenyl or C₂-C₄ haloalkenyl; R³ and R⁴are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is C₁-C₄-alkoxy; R³ and R⁴ are both hydrogen;and X is N, CH, or CF.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄ alkoxy;

R³ and R⁴ are both hydrogen; X is N, CH, or CF; R⁵ is hydrogen or F; R⁶is hydrogen or F; R^(6′) is hydrogen; R^(6″), if applicable to therelevant A group, is hydrogen or halogen; and R⁷ and R^(7′), ifapplicable to the relevant A group, are independently hydrogen orhalogen.

In some embodiments, R² is halogen, C₁-C₄-alkoxy, or C₂-C₄-alkenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is one of groups A1 toA20.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; X is N, CH,or CF; A is one of groups A1 to A20; R⁵ is hydrogen or F; R⁶ and R^(6′)are independently hydrogen or F; and R⁷ and R^(7′), if applicable to therelevant A group, are independently hydrogen, halogen, C₁-C₄ alkyl, orC₁-C₄ haloalkyl.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; and X is N, CH, or CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is N,CH, or CF.

In some embodiments, R² is vinyl or 1-propenyl; R³ and R⁴ are hydrogen;and X is N, CH, or CF.

In some embodiments, R² is methoxy; R³ and R⁴ are hydrogen; and X is N,CH, or CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is N.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X isCH.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X isCF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; X is CF; Ais one of A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15; R⁵ is F; and R⁶is H.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is one of A21 to A36.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is CF; and A is one of

wherein R⁵ is hydrogen or F.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is

where R⁵ is hydrogen or F.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is CF; and A is

In some embodiments, the pyridine carboxylic acid herbicide can comprisea compound defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof,

with the proviso that the pyridine carboxylic acid herbicide is not acompound defined by Formula (I)

wherein

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl;

R² is chlorine;

R³ and R⁴ are hydrogen;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, OH, amino, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃alkylamino, or cyclopropyl;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, OH, NH₂, CN,C₁-C₃ alkyl, C₁-C₃ alkoxy, cyclopropyl, or vinyl;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃alkoxy, C₁-C₃ alkylthio, cyclopropyl, C₁-C₃ alkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₃ alkyl, phenyl, or C₁-C₃ alkylcarbonyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is CY, wherein Y is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Ais A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is C₅-C₈ alkyl or C₇-C₁₀arylalkyl, and R^(1″) and R^(1′″) are independently hydrogen, C₁-C₁₂alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is F, Br, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33,A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halocyclopropyl, C₂-C₄ alkenyl,C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio,C₁-C₃ haloalkylthio, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently C₁-C₄ alkyl, C₁-C₄ haloalkyl,halocyclopropyl, C₃-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₄ alkylamino orC₂-C₄ haloalkylamino, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, or A18;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently C₁-C₄ alkyl, C₁-C₄ haloalkyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃haloalkoxy, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄haloalkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A3, A6, A11, A12, A15, A18, A19, or A20;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is C₃-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl,C₃-C₆ alkynyl, formyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ trialkylsilyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (II):

wherein

R¹ is OR^(1′) or NR^(1″)R^(1″), wherein R^(1′) is hydrogen, C₁-C₈ alkyl,or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments:

R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, or C₁-C₄ haloalkylthio;

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino;

A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15, A21, A22,A23, A24, A27, A28, A29, A30, A31, or A32;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl,C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄haloalkylamino;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl,amino or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄-alkoxy. In certain embodiments, R² is Cl, methoxy, vinyl, or1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15.In certain embodiments, A is A1, A2, A3, A13, A14, or A15. In certainembodiments, A is A15.

In some embodiments, R⁵ is hydrogen or F. In certain embodiments, R⁵ isF. In certain embodiments, R⁵ is H.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ isF. In certain embodiments, R⁶ is H. In some embodiments, R^(6″) ishydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄alkynyl, CN, or NO₂. In certain embodiments, R⁶, R^(6′), and R^(6″) areall hydrogen.

In certain embodiments, R² is Cl, methoxy, vinyl, or 1-propenyl; R³ andR⁴ are hydrogen; A is A15; R⁵ is hydrogen or F; R⁶ is hydrogen or F; andR^(6″) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (III):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″), wherein R^(1′) is hydrogen, C₁-C₈ alkyl,or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments:

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₂-C₁₀arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, or C₁-C₄ haloalkylthio;

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl,amino or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. Insome embodiments, X is CH. In some embodiments, X is CF. In otherembodiments, X is C—CH₃.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄-alkoxy. In certain embodiments, R² is Cl, methoxy, vinyl, or1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ isF. In certain embodiments, R⁶ is H. In some embodiments, R^(6′) ishydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄alkynyl, CN, or NO₂. In certain embodiments, R⁶ and R^(6′) are bothhydrogen.

In certain embodiments, R⁷ and R^(7′) are both hydrogen.

In certain embodiments, R⁶, R^(6′), R⁷, and R^(7′) are all hydrogen.

In certain embodiments, X is CF, R¹ is OR^(1′), wherein R^(1′) ishydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl; R² is Cl, methoxy, vinyl, or1-propenyl; R³ and R⁴ are hydrogen; R⁶ is hydrogen or F; and R^(6′) ishydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise one of Compounds 1-24, the structures of which are shown in thetable below.

Compound No. Structure  1

 2

 3

 4

 5

 6

 7

 8

 9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinicacid, or an agriculturally acceptable N-oxide, salt, or ester thereof.

In some embodiments, the pyridine carboxylic acid herbicide can beprovided as an agriculturally acceptable salt. Exemplary agriculturallyacceptable salts of the pyridine carboxylic acid herbicides of Formula(I) include, but are not limited to, sodium salts, potassium salts,ammonium salts or substituted ammonium salts, in particular mono-, di-and tri-C₁-C₈ alkylammonium salts such as methyl ammonium,dimethylammonium and isopropylammonium, mono-, di- andtri-hydroxy-C₂-C₈-alkylammonium salts such as hydroxyethylammonium,di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium,hydroxypropylammonium, di(hydroxypropyl)ammonium andtri(hydroxypropyl)ammonium salts, olamine salts, diglycolamine salts,choline salts, and quaternary ammonium salts such as those representedby the formula R⁹R¹⁰R¹¹R¹²N⁺ and wherein R⁹, R¹⁰, R¹¹ and R¹² (e.g.,R⁹-R¹²) each independently can represent hydrogen, C₁-C₁₀ alkyl, C₂-C₈alkenyl, C₂-C₈ alkynyl, C₁-C₈ alkoxy, C₁-C₈ alkylthio, or aryl groups,provided that R⁹-R¹² are sterically compatible.

In some embodiments, the pyridine carboxylic acid herbicide can beprovided as an agriculturally acceptable ester. Suitable esters include,but are not limited to, C₁-C₈-alkyl esters and C₁-C₄-alkoxy-C₂-C₄-alkylesters, such as methyl esters, ethyl esters, isopropyl, butyl, hexyl,heptyl, isoheptyl, isooctyl, 2-ethylhexyl, butoxyethyl esters,substituted or unsubstituted aryl esters, orthoesters, substituted orunsubstituted alkylaryl esters, and substituted or unsubstitutedarylalkyl esters. In some embodiments, the ester can comprise a C₁-C₈alkyl ester, wherein the C₁-C₈ alkyl group is optionally substitutedwith one or more moieties selected from the group consisting of cyano,C₂-C₈ alkoxy, and C₂-C₈ alkylsulfonyl. For example, the ester cancomprise a methyl, —CH₂CN, —CH₂OCH₃, —CH₂OCH₂CH₂OCH₃, or —CH₂CH₂SO₂CH₃ester.

The ester can also be an acetal (e.g., a cyclic acetal) formed byprotection of the carbonyl group in the pyridine carboxylic acidherbicides described above (e.g., by Formula (I)). For example, thepyridine carboxylic acid herbicides described above can be reacted witha suitable diol (e.g., a diol such as ethane-1,2-diol orbutane-2,3-diol, for example, using standard protecting group chemistry,such as taught in Greene, et al., Protective Groups in OrganicSynthesis, John Wiley and Sons, Fourth Edition, 2007, herebyincorporated by reference) to form a cyclic acetal. In one embodiment,the ester can be a cyclic acetal defined by the structure below, whereR², R³, R⁴, X, and A are as described above.

In some embodiments, the ester can comprise a substituted orunsubstituted benzyl ester. In some embodiments, the ester can comprisea benzyl ester optionally substituted with one or more moieties selectedfrom the group consisting of halogen, C₁-C₂ alkyl, C₁-C₂ haloalkyl, andcombinations thereof. In some embodiments, the ester can comprise amethyl ester.

The pyridine carboxylic acid herbicide, or an agriculturally acceptableN-oxide, salt, or ester thereof, can be applied to vegetation or an areaadjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount sufficient to induce aherbicidal effect. In some embodiments, the pyridine carboxylic acidherbicide, or an agriculturally acceptable N-oxide, salt, or esterthereof, is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 0.1 grams or greater of acid equivalent perhectare (g ae/ha) (e.g., 0.2 g ae/ha or greater, 0.3 g ae/ha or greater,0.4 g ae/ha or greater, 0.5 g ae/ha or greater, 0.6 g ae/ha or greater,0.7 g ae/ha or greater, 0.8 g ae/ha or greater, 0.9 g ae/ha or greater,1 g ae/ha or greater, 1.1 g ae/ha or greater, 1.2 g ae/ha or greater,1.3 g ae/ha or greater, 1.4 g ae/ha or greater, 1.5 g ae/ha or greater,1.6 g ae/ha or greater, 1.7 g ae/ha or greater, 1.8 g ae/ha or greater,1.9 g ae/ha or greater, 2 g ae/ha or greater, 2.25 g ae/ha or greater,2.5 g ae/ha or greater, 2.75 g ae/ha or greater, 3 g ae/ha or greater, 4g ae/ha or greater, 5 g ae/ha or greater, 6 g ae/ha or greater, 7 gae/ha or greater, 8 g ae/ha or greater, 9 g ae/ha or greater, 10 g ae/haor greater, 11 g ae/ha or greater, 12 g ae/ha or greater, 13 g ae/ha orgreater, 14 g ae/ha or greater, 15 g ae/ha or greater, 16 g ae/ha orgreater, 17 g ae/ha or greater, 18 g ae/ha or greater, 19 g ae/ha orgreater, 20 g ae/ha or greater, 21 g ae/ha or greater, 22 g ae/ha orgreater, 23 g ae/ha or greater, 24 g ae/ha or greater, 25 g ae/ha orgreater, 26 g ae/ha or greater, 27 g ae/ha or greater, 28 g ae/ha orgreater, 29 g ae/ha or greater, 30 g ae/ha or greater, 31 g ae/ha orgreater, 32 g ae/ha or greater, 33 g ae/ha or greater, 34 g ae/ha orgreater, 35 g ae/ha or greater, 36 g ae/ha or greater, 37 g ae/ha orgreater, 38 g ae/ha or greater, 39 g ae/ha or greater, 40 g ae/ha orgreater, 41 g ae/ha or greater, 42 g ae/ha or greater, 43 g ae/ha orgreater, 44 g ae/ha or greater, 45 g ae/ha or greater, 46 g ae/ha orgreater, 47 g ae/ha or greater, 48 g ae/ha or greater, 49 g ae/ha orgreater, 50 g ae/ha or greater, 55 g ae/ha or greater, 60 g ae/ha orgreater, 65 g ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha orgreater, 80 g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha orgreater, 95 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha orgreater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g ae/ha orgreater, 150 g ae/ha or greater, 160 g ae/ha or greater, 170 g ae/ha orgreater, 180 g ae/ha or greater, 190 g ae/ha or greater, 200 g ae/ha orgreater, 210 g ae/ha or greater, 220 g ae/ha or greater, 230 g ae/ha orgreater, 240 g ae/ha or greater, 250 g ae/ha or greater, 260 g ae/ha orgreater, 270 g ae/ha or greater, 280 g ae/ha or greater, or 290 g ae/haor greater).

In some embodiments, the pyridine carboxylic acid herbicide, or anagriculturally acceptable N-oxide, salt, or ester thereof, is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of300 g ae/ha or less (e.g., 290 g ae/ha or less, 280 g ae/ha or less, 270g ae/ha or less, 260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/haor less, 230 g ae/ha or less, 220 g ae/ha or less, 210 g ae/ha or less,200 g ae/ha or less, 190 g ae/ha or less, 180 g ae/ha or less, 170 gae/ha or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha orless, 130 g ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100g ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha orless, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or less, 65 gae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less, 50 g ae/ha orless, 49 g ae/ha or less, 48 g ae/ha or less, 47 g ae/ha or less, 46 gae/ha or less, 45 g ae/ha or less, 44 g ae/ha or less, 43 g ae/ha orless, 42 g ae/ha or less, 41 g ae/ha or less, 40 g ae/ha or less, 39 gae/ha or less, 38 g ae/ha or less, 37 g ae/ha or less, 36 g ae/ha orless, 35 g ae/ha or less, 34 g ae/ha or less, 33 g ae/ha or less, 32 gae/ha or less, 31 g ae/ha or less, 30 g ae/ha or less, 29 g ae/ha orless, 28 g ae/ha or less, 27 g ae/ha or less, 26 g ae/ha or less, 25 gae/ha or less, 24 g ae/ha or less, 23 g ae/ha or less, 22 g ae/ha orless, 21 g ae/ha or less, 20 g ae/ha or less, 19 g ae/ha or less, 18 gae/ha or less, 17 g ae/ha or less, 16 g ae/ha or less, 15 g ae/ha orless, 14 g ae/ha or less, 13 g ae/ha or less, 12 g ae/ha or less, 11 gae/ha or less, 10 g ae/ha or less, 9 g ae/ha or less, 8 g ae/ha or less,7 g ae/ha or less, 6 g ae/ha or less, 5 g ae/ha or less, 4 g ae/ha orless, 3 g ae/ha or less, 2.75 g ae/ha or less, 2.5 g ae/ha or less, 2.25g ae/ha or less, 2 g ae/ha or less, 1.9 g ae/ha or less, 1.8 g ae/ha orless, 1.7 g ae/ha or less, 1.6 g ae/ha or less, 1.5 g ae/ha or less, 1.4g ae/ha or less, 1.3 g ae/ha or less, 1.2 g ae/ha or less, 1.1 g ae/haor less, 1 g ae/ha or less, 0.9 g ae/ha or less, 0.8 g ae/ha or less,0.7 g ae/ha or less, 0.6 g ae/ha or less, 0.5 g ae/ha or less, 0.4 gae/ha or less, 0.3 g ae/ha or less, or 0.2 g ae/ha or less).

The pyridine carboxylic acid herbicide, or an agriculturally acceptableN-oxide, salt, or ester thereof, can be applied to vegetation or an areaadjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount ranging from any of theminimum values described above to any of the maximum values describedabove. In some embodiments, the pyridine carboxylic acid herbicide, oran agriculturally acceptable N-oxide, salt, or ester thereof, is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount offrom 0.1-300 g ae/ha (e.g., from 0.1-5 g ae/ha, from 2.5-40 g ae/ha,from 0.1-40 g ae/ha, from 0.1-2.5 g ae/ha, from 2-150 g ae/ha, from 5-75g ae/ha, from 5-40 g ae/ha, from 30-40 g ae/ha, or from 5-15 g ae/ha).In some embodiments, the pyridine carboxylic acid herbicide, or anagriculturally acceptable N-oxide, salt, or ester thereof, is applied inan amount from 30-40 g ae/ha.

Azole Carboxylate Safeners

In addition to the pyridine carboxylic acid herbicide, the compositionscan further include an azole carboxylate safener, or an agriculturallyacceptable salt or ester thereof. Herbicide safeners are molecules usedin combination with herbicides to make them “safer”—that is, to reducethe effect of the herbicide on crop plants and to improve selectivitybetween crop plants and weed species being targeted by the herbicide.Herbicide safeners can be used to pre-treat crop seeds prior to plantingor they can be sprayed on plants as a mixture with the herbicide.

Azoles are a class of five-membered nitrogen heterocyclic ring compoundscontaining at least one additional heteroatom (e.g., nitrogen, sulfur,or oxygen) within the heterocyclic ring. Examples of azoles include, forexample, pyrazoles, imidazoles, thiazoles, oxazoles, isoxazoles andtriazoles.

Azole carboxylate safeners are a class of safeners based oncarboxylate-substituted azole moieties. Examples of azole carboxylatesafeners include pyrazole carboxylate safeners, imidazole carboxylatesafeners, thiazole carboxylate safeners, oxazole carboxylate safeners,isoxazole carboxylate safeners, and triazole carboxylate safeners. Insome embodiments, the composition can include an azole carboxylatesafener selected from the group consisting of fenchlorazole, isoxadifen,mefenpyr and agriculturally acceptable salts and esters thereof, or acombination thereof. In some embodiments, the azole carboxylate safenercan include fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, orcombinations thereof.

In some embodiments, the azole carboxylate safener can comprisefenchlorazole, shown below, or an agriculturally acceptable salt orester thereof.

In some embodiments, the fenchlorazole is provided as an agriculturallyacceptable salt or ester. An exemplary agriculturally acceptable esterof fenchlorazole is fenchlorazole ethyl, shown below.

In some embodiments, the azole carboxylate safener can compriseisoxadifen, shown below, or an agriculturally acceptable salt or esterthereof.

In some embodiments, the isoxadifen is provided as an agriculturallyacceptable salt or ester. An exemplary agriculturally acceptable esterof isoxadifen is isoxadifen-ethyl, shown below.

In some embodiments, the azole carboxylate safener can comprisemefenpyr, shown below, or an agriculturally acceptable salt or esterthereof.

In some embodiments, the mefenpyr is provided as an agriculturallyacceptable salt or ester. An exemplary agriculturally acceptable esterof mefenpyr is mefenpyr-diethyl, shown below.

The azole carboxylate safener or an agriculturally acceptable salt orester thereof can be used in an amount sufficient to induce a safeningeffect. In some embodiments the azole carboxylate safener or anagriculturally acceptable salt or ester thereof is applied to vegetationor an area adjacent the vegetation or applied to soil or water in anamount of 1 grams or greater of acid equivalent per hectare (g ai/ha)(e.g., 2 g ai/ha or greater, 3 g ai/ha or greater, 4 g ai/ha or greater,5 g ai/ha or greater, 6 g ai/ha or greater, 7 g ai/ha or greater, 8 gai/ha or greater, 9 g ai/ha or greater, 10 g ai/ha or greater, 11 gai/ha or greater, 12 g ai/ha or greater, 13 g ai/ha or greater, 14 gai/ha or greater, 15 g ai/ha or greater, 16 g ai/ha or greater, 17 gai/ha or greater, 18 g ai/ha or greater, 19 g ai/ha or greater, 20 gai/ha or greater, 21 g ai/ha or greater, 22 g ai/ha or greater, 23 gai/ha or greater, 24 g ai/ha or greater, 25 g ai/ha or greater, 26 gai/ha or greater, 27 g ai/ha or greater, 28 g ai/ha or greater, 29 gai/ha or greater, 30 g ai/ha or greater, 31 g ai/ha or greater, 32 gai/ha or greater, 33 g ai/ha or greater, 34 g ai/ha or greater, 35 gai/ha or greater, 36 g ai/ha or greater, 37 g ai/ha or greater, 38 gai/ha or greater, 39 g ai/ha or greater, 40 g ai/ha or greater, 41 gai/ha or greater, 42 g ai/ha or greater, 43 g ai/ha or greater, 44 gai/ha or greater, 45 g ai/ha or greater, 46 g ai/ha or greater, 47 gai/ha or greater, 48 g ai/ha or greater, 49 g ai/ha or greater, 50 gai/ha or greater, 55 g ai/ha or greater, 60 g ai/ha or greater, 65 gai/ha or greater, 70 g ai/ha or greater, 75 g ai/ha or greater, 80 gai/ha or greater, 85 g ai/ha or greater, 90 g ai/ha or greater, 95 gai/ha or greater, 100 g ai/ha or greater, 110 g ai/ha or greater, 120 gai/ha or greater, 130 g ai/ha or greater, 140 g ai/ha or greater, 150 gai/ha or greater, 160 g ai/ha or greater, 170 g ai/ha or greater, 180 gai/ha or greater, 190 g ai/ha or greater, 200 g ai/ha or greater, 210 gai/ha or greater, 220 g ai/ha or greater, 230 g ai/ha or greater, 240 gai/ha or greater, 250 g ai/ha or greater, 260 g ai/ha or greater, 270 gai/ha or greater, 280 g ai/ha or greater, or 290 g ai/ha or greater).

In some embodiments the azole carboxylate safener or an agriculturallyacceptable salt or ester thereof is applied to vegetation or an areaadjacent the vegetation or applied to soil or water in an amount of 300g ai/ha or less (e.g., 290 g ai/ha or less, 280 g ai/ha or less, 270 gai/ha or less, 260 g ai/ha or less, 250 g ai/ha or less, 240 g ai/ha orless, 230 g ai/ha or less, 220 g ai/ha or less, 210 g ai/ha or less, 200g ai/ha or less, 190 g ai/ha or less, 180 g ai/ha or less, 170 g ai/haor less, 160 g ai/ha or less, 150 g ai/ha or less, 140 g ai/ha or less,130 g ai/ha or less, 120 g ai/ha or less, 110 g ai/ha or less, 100 gai/ha or less, 95 g ai/ha or less, 90 g ai/ha or less, 85 g ai/ha orless, 80 g ai/ha or less, 75 g ai/ha or less, 70 g ai/ha or less, 65 gai/ha or less, 60 g ai/ha or less, 55 g ai/ha or less, 50 g ai/ha orless, 49 g ai/ha or less, 48 g ai/ha or less, 47 g ai/ha or less, 46 gai/ha or less, 45 g ai/ha or less, 44 g ai/ha or less, 43 g ai/ha orless, 42 g ai/ha or less, 41 g ai/ha or less, 40 g ai/ha or less, 39 gai/ha or less, 38 g ai/ha or less, 37 g ai/ha or less, 36 g ai/ha orless, 35 g ai/ha or less, 34 g ai/ha or less, 33 g ai/ha or less, 32 gai/ha or less, 31 g ai/ha or less, 30 g ai/ha or less, 29 g ai/ha orless, 28 g ai/ha or less, 27 g ai/ha or less, 26 g ai/ha or less, 25 gai/ha or less, 24 g ai/ha or less, 23 g ai/ha or less, 22 g ai/ha orless, 21 g ai/ha or less, 20 g ai/ha or less, 19 g ai/ha or less, 18 gai/ha or less, 17 g ai/ha or less, 16 g ai/ha or less, 15 g ai/ha orless, 14 g ai/ha or less, 13 g ai/ha or less, 12 g ai/ha or less, 11 gai/ha or less, 10 g ai/ha or less, 9 g ai/ha or less, 8 g ai/ha or less,7 g ai/ha or less, 6 g ai/ha or less, 5 g ai/ha or less, 4 g ai/ha orless, 3 g ai/ha or less, or 2 g ai/ha or less).

The azole carboxylate safener or an agriculturally acceptable salt orester thereof can be applied to vegetation or an area adjacent thevegetation or applied to soil or water in an amount ranging from any ofthe minimum values described above to any of the maximum valuesdescribed above. In some embodiments, the azole carboxylate safener oragriculturally acceptable salt or ester thereof is applied to vegetationor an area adjacent the vegetation or applied to soil or water in anamount of from 1-300 g ai/ha (e.g., from 2-150 g ai/ha, from 5-75 gai/ha, from 5-40 g ai/ha, from 30-40 g ai/ha, or from 5-15 g ai/ha). Insome embodiments, the azole carboxylate safener or agriculturallyacceptable salt or ester thereof is applied in an amount from 30-40 gai/ha.

II. COMPOSITIONS

A. Herbicidal Mixtures or Combinations

The (a) pyridine carboxylic acid herbicide, or an agriculturallyacceptable N-oxide, salt, or ester thereof, can be mixed with or appliedin combination with (b) an azole carboxylate safener or anagriculturally acceptable salt or ester thereof.

In some embodiments, the (a) pyridine carboxylic acid herbicide, or anagriculturally acceptable N-oxide, salt, or ester thereof, can be mixedwith or applied in combination with (b) an azole carboxylate safener oran agriculturally acceptable salt or ester thereof in an amountsufficient to induce a synergistic effect. In some embodiments, (a) and(b) are used in an amount sufficient to induce a synergistic herbicidaleffect while still showing good crop compatibility (i.e., their use incrops does not result in increased damage to crops or reduces damage tocrops when compared to the individual application of the herbicidalcompounds (a) or (b)).

As described in the Herbicide Handbook of the Weed Science Society ofAmerica, Tenth Edition, 2014, p. 487, “‘synergism’ [is] an interactionof two or more factors such that the effect when combined is greaterthan the predicted effect based on the response to each factor appliedseparately.” Synergistic in the herbicide context can mean that the useof (a) and (b) as defined above results in an increased weed controleffect compared to the weed control effects that are possible with theuse of (a) or (b) alone. In some embodiments, the damage or injury tothe undesired vegetation or the crop caused by the compositions andmethods disclosed herein is evaluated using a scale from 0% to 100%,when compared with the untreated control vegetation, wherein 0%indicates no damage to the undesired vegetation and 100% indicatescomplete destruction of the undesired vegetation. In some embodiments,Colby's formula is applied to determine whether using (a) and (b) incombination shows a synergistic effect: S. R. Colby, CalculatingSynergistic and Antagonistic Responses of Herbicide Combinations, W EEDS15, p. 22 (1967)

$E = {X + Y - \frac{X*Y}{100}}$

wherein

X=effect in percent using (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof at anapplication rate a;

Y=effect in percent using (b) an azole carboxylate safener or anagriculturally acceptable salt or ester thereof at an application rateb;

E=expected effect (in %) of (a)+(b) at application rates a and b.

In Colby's equation, the value E corresponds to the effect (plant damageor injury) that is to be expected if the activity of the individualcompounds is additive. If the observed effect is higher than the value Ecalculated according to the Colby equation, then a synergistic effect ispresent according to the Colby equation. Likewise, with respect to thedesired crop, if the observed effect is lower than the value Ecalculated according to the Colby equation, then a synergistic effect ispresent according to the Colby equation with respect to crop safening.

In some embodiments, the compositions and methods disclosed herein aresynergistic as defined by the Colby equation. In some embodiments, thejoint action of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof and (b) anazole carboxylate safener or an agriculturally acceptable salt or esterthereof results in enhanced activity against undesired vegetation (viasynergism), even at application rates below those typically used for thepesticide to have a herbicidal effect on its own. In some embodiments,the compositions and methods disclosed herein can, based on theindividual components, be used at lower application rates to achieve aherbicidal effect comparable to the effect produced by the individualcomponents at normal application rates. In some embodiments, thecompositions and methods disclosed herein provide an accelerated actionon undesired vegetation (i.e. they effect damaging of undesiredvegetation more quickly compared with application of the individualherbicides). In some embodiments, the joint action of (a) a pyridinecarboxylic acid herbicide or an agriculturally acceptable N-oxide, salt,or ester thereof and (b) azole carboxylate safener or an agriculturallyacceptable salt or ester thereof results in reduced activity againstdesired vegetation/crops (via synergism).

In some embodiments, the observed effect for undesired vegetation is atleast 1%, at least 2%, at least 3%, at least 4%, at least 5%, at least10%, at least 15%, at least 20%, or at least 25% greater than the effect(E) calculated according to the Colby equation (e.g., an observed effectof 96% would be 4% greater than an calculated effect (E) of 92%). Insome embodiments, for undesired vegetation, the difference (D_(O))between 100% and the observed effect is at least 5%, at least 10%, atleast 15%, at least 20%, at least 25%, at least 30%, at least 35%, atleast 40%, at least 45%, or at least 50% less than the difference(D_(E)) between 100% and the effect (E) calculated according to theColby equation (e.g., an observed effect of 96% would produce a D_(O) of4%, a calculated effect (E) of 92% would produce a D_(E) of 8%, andD_(O) would be 50% less than or half of D_(E)). In some embodiments, theobserved effect for desired vegetation/crops is at least 1%, at least2%, at least 3%, at least 4%, at least 5%, at least 6%, at least 7%, atleast 8%, at least 9%, or at least 10% less than the effect (E)calculated according to the Colby equation. In some embodiments, fordesired vegetation/crops, the difference (D_(O)) between 100% and theobserved effect is at least 2%, at least 5%, at least 10%, at least 15%,at least 20%, or at least 25% greater than the difference (D_(E))between 100% and the effect (E) calculated according to the Colbyequation.

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) an azole carboxylate safener, or anagriculturally acceptable salt or ester thereof (in g ai/ha) is 1:5 ormore (e.g., 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more,1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 ormore, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more,1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more,1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 ormore, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.25:1or more, 2.5:1 or more, 2.75:1 or more, 3:1 or more, 3.25:1 or more,3.5:1 or more, 3.75:1 or more, 4:1 or more, 4.25:1 or more, 4.5:1 ormore, 4.75:1 or more, 5:1 or more, 6:1 or more, 7:1 or more, 8:1 ormore, 9:1 or more, 10:1 or more, 11:1 or more, 12:1 or more, 13:1 ormore, 14:1 or more, 15:1 or more, 16:1 or more, 17:1 or more, 18:1 ormore, 19:1 or more, 20:1 or more, 25:1 or more, 30:1 or more, 35:1 ormore, 40:1 or more, 45:1 or more, 50:1 or more, 55:1 or more, or 60:1 ormore).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) an azole carboxylate safener or anagriculturally acceptable salt or ester thereof (in g ai/ha) is 65:1 orless (e.g., 60:1 or less, 55:1 or less, 50:1 or less, 45:1 or less, 40:1or less, 35:1 or less, 30:1 or less, 25:1 or less, 20:1 or less, 19:1 orless, 18:1 or less, 17:1 or less, 16:1 or less, 15:1 or less, 14:1 orless, 13:1 or less, 12:1 or less, 11:1 or less, 10:1 or less, 9:1 orless, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less, 4.75:1 orless, 4.5:1 or less, 4.25:1 or less, 4:1 or less, 3.75:1 or less, 3.5:1or less, 3.25:1 or less, 3:1 or less, 2.75:1 or less, 2.5:1 or less,2.25:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 orless, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less,1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 orless, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, or 1:4.75 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof (in g ae/ha)to (b) an azole carboxylate safener or an agriculturally acceptable saltor ester thereof (in g ae/ha) can range from any of the minimum ratiosdescribed above to any of the maximum values described above. In someembodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) an azole carboxylate safener or anagriculturally acceptable salt or ester thereof (in g ai/ha) is from65:1 to 1:5 (e.g., from 60:1 to 1:5, from 55:1 to 1:5, from 50:1 to 1:5,from 45:1 to 1:5, from 40:1 to 1:5, from 35:1 to 1:5, from 30:1 to 1:5,from 25:1 to 1:5, from 20:1 to 1:5, from 15:1 to 1:5, from 10:1 to 1:5,from 5:1 to 1:5, 4.5:1 to 1:4.5, from 4:1 to 1:4, from 1:1 to 1:4, from3.5:1 to 1:3.5, from 3:1 to 1:3, from 2.5:1 to 1:2.5, from 2:1 to 1:2,from 1.9:1 to 1:1.9, from 1.8:1 to 1:1.8, from 1.7:1 to 1:1.7, from1.6:1 to 1:1.6, from 1.5:1 to 1:1.5, from 1.4:1 to 1:1.4, from 1.3:1 to1:1.3, from 1.2:1 to 1:1.2, from 1.1:1 to 1:1.1). In some embodiments,the weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof (in g ae/ha)to (b) an azole carboxylate safener, or an agriculturally acceptablesalt or ester thereof (in g ai/ha) is 1:1.

In some examples, the active ingredients in the compositions disclosedherein consist of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof and (b) anazole carboxylate safener or an agriculturally acceptable salt or esterthereof.

B. Formulations

The present disclosure also relates to formulations of the compositionsand methods disclosed herein. In some embodiments, the formulation canbe in the form of a single package formulation including both (a) apyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof and (b) an azole carboxylate safener, oran agriculturally acceptable salt or ester thereof. In some embodiments,the formulation can be in the form of a single package formulationincluding both (a) and (b) and further including at least one additive.In some embodiments, the formulation can be in the form of a two-packageformulation, wherein one package contains (a) and optionally at leastone additive while the other package contains (b) and optionally atleast one additive. In some embodiments of the two-package formulation,the formulation including (a) and optionally at least one additive andthe formulation including (b) and optionally at least one additive aremixed before application and then applied simultaneously. In someembodiments, the mixing is performed as a tank mix (i.e., theformulations are mixed immediately before or upon dilution with water).In some embodiments, the formulation including (a) and the formulationincluding (b) are not mixed but are applied sequentially (insuccession), for example, immediately or within 1 hour, within 2 hours,within 4 hours, within 8 hours, within 16 hours, within 24 hours, within2 days, or within 3 days, of each other.

In some embodiments, the formulation of (a) and (b) is present insuspended, emulsified, or dissolved form. Exemplary formulationsinclude, but are not limited to, aqueous solutions, powders,suspensions, also highly-concentrated aqueous, oily or other suspensionsor dispersions, aqueous emulsions, aqueous microemulsions, aqueoussuspo-emulsions, oil dispersions, self-emulsifying formulations, pastes,dusts, and materials for spreading or granules.

In some embodiments, (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof and/or (b) anazole carboxylate safener, or an agriculturally acceptable salt or esterthereof is an aqueous solution that can be diluted before use. In someembodiments, (a) and/or (b) is provided as a high-strength formulationsuch as a concentrate. In some embodiments, the concentrate is stableand retains potency during storage and shipping. In some embodiments,the concentrate is a clear, homogeneous liquid that is stable attemperatures of 54° C. or greater. In some embodiments, the concentratedoes not exhibit any precipitation of solids at temperatures of −10° C.or higher. In some embodiments, the concentrate does not exhibitseparation, precipitation, or crystallization of any components at lowtemperatures. For example, the concentrate remains a clear solution attemperatures below 0° C. (e.g., below −5° C., below −10° C., below −15°C.). In some embodiments, the concentrate exhibits a viscosity of lessthan 50 centipoise (50 megapascals), even at temperatures as low as 5°C.

The compositions and methods disclosed herein can also be mixed with orapplied with an additive. In some embodiments, the additive can bediluted in water or can be concentrated. In some embodiments, theadditive is added sequentially. In some embodiments, the additive isadded simultaneously. In some embodiments, the additive is premixed withthe pyridine carboxylic acid herbicide or agriculturally acceptableN-oxide, salt, or ester thereof. In some embodiments, the additive ispremixed with the azole carboxylate safener or agriculturally acceptablesalt or ester thereof.

C. Other Actives

In some embodiments, the additive is an additional pesticide. Forexample, the compositions described herein can be applied in conjunctionwith one or more additional herbicides to control undesirablevegetation. The composition can be formulated with the one or moreadditional herbicides, tank mixed with the one or more additionalherbicides, or applied sequentially with the one or more additionalherbicides. Exemplary additional herbicides include, but are not limitedto: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 2,4-D choline salt, 2,4-D esters andamines, 2,4-DB, 3,4-DA, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA,2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein,alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione,ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor,4-aminopicolinic acid based herbicides, such as halauxifen,halauxifen-methyl,4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylicacid, benzyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate,and those described in U.S. Pat. Nos. 7,314,849 and 7,432,227 to Balko,et al., aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate,anilofos, anisuron, asulam, atraton, atrazine, azafenidin, aziprotryne,barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,benfuresate, bensulide, benthiocarb, bentazon-sodium, benzadox,benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor,benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, borax,bromacil, bromobonil, bromobutide, bromofenoxim, brompyrazon, butachlor,butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin,butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calciumchlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide,carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, CEPC,chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine,chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop,chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen,chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham,chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin,cisanilide, clacyfos, clethodim, cliodinate, clodinafop-propargyl,clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid,cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol,cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate,cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat,cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor,desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea,dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam,diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon,dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb,diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC,DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb,ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate,ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, etinofen,etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop,fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone,fenquinotrione, fenteracol, fenthiaprop, fentrazamide, fenuron, ferroussulfate, flamprop, flamprop-M, fluazifop, fluazifop-P-butyl, fluazolate,flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican,flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin,flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine,fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate,flupyrsulfuron, fluridone, flurochloridone, fluroxypyr,fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron,fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium,glufosinate-P-ammonium, glyphosate salts and esters, halosafen,haloxydine, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz,imazapic, imazapyr, imazaquin, indanofan, indaziflam, iodobonil,iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron,ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil,isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon,isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop,karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPAesters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P,medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron,mesotrione, metam, metamifop, metamitron, metazachlor, metflurazon,methabenzthiazuron, methalpropalin, methazole, methiobencarb,methiozolin, methiuron, methometon, methoprotryne, methyl bromide,methyl isothiocyanate, methyldymron, metobenzuron, metobromuron,metolachlor, metosulam, metoxuron, metribuzin, molinate, monalide,monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat,MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon,nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen,norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, oryzalin,oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone,oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate,pelargonic acid, pendimethalin, pentachlorophenol, pentanochlor,pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham,phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram,picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide,potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine,prodiamine, profluazol, profluralin, profoxydim, proglinazine,prohexadione-calcium, prometon, prometryn, pronamide, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propyzamide, prosulfalin, prosulfocarb, prosulfuron,proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl,pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyributicarb,pyriclor, pyridafol, pyridate, pyrithiobac-sodium, pyroxasulfone,quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop,quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil,S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine,simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate,sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate,sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam,tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil,terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn,tetrafluron, thenylchlor, thiameturon, thiazafluron, thiazopyr,thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron,thifensulfurn-methyl, thiobencarb, tiafenacil, tiocarbazil, tioclorim,tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone,triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba,triclopyr choline salt, triclopyr esters and amines, tridiphane,trietazine, trifloxysulfuron, trifludimoxazin, trifluralin,triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon,tripropindan, tritac, tritosulfuron, vernolate, xylachlor and salts,esters, optically active isomers, and mixtures thereof.

In some embodiments, the additional pesticide or an agriculturallyacceptable salt or ester thereof is provided in a premixed formulationwith (a), (b), or combinations thereof. In some embodiments, thepyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof is provided in a premixed formulationwith an additional pesticide. In some embodiments, the azole carboxylatesafener or an agriculturally acceptable salt or ester thereof isprovided in a premixed formulation with an additional pesticide.

D. Adjuvants/Carriers/Colorants/Adhesives

In some embodiments, the additive includes an agriculturally acceptableadjuvant. Exemplary agriculturally acceptable adjuvants include, but arenot limited to, antifreeze agents, antifoam agents, compatibilizingagents, sequestering agents, neutralizing agents and buffers, corrosioninhibitors, colorants, odorants, penetration aids, wetting agents,spreading agents, dispersing agents, thickening agents, freeze pointdepressants, antimicrobial agents, crop oil, herbicide safeners,adhesives (for instance, for use in seed formulations), surfactants,protective colloids, emulsifiers, tackifiers, and mixtures thereof.Exemplary agriculturally acceptable adjuvants include, but are notlimited to, crop oil concentrate (mineral oil (85%)+emulsifiers (15%));nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammoniumsalt; blend of petroleum hydrocarbon, alkyl esters, organic acid, andanionic surfactant; C₉-C₁₁ alkylpolyglycoside; phosphate alcoholethoxylate; natural primary alcohol (C₁₂-C₁₆) ethoxylate;di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated seedoil; tridecyl alcohol (synthetic) ethoxylate (8 EO); tallow amineethoxylate (15 EO); and PEG(400) dioleate-99.

In some embodiments, the additive can be an additional safener.

Exemplary surfactants (e.g., wetting agents, tackifiers, dispersants,emulsifiers) include, but are not limited to, the alkali metal salts,alkaline earth metal salts and ammonium salts of aromatic sulfonicacids, for example lignosulfonic acids, phenolsulfonic acids,naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid, and offatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene or of the naphthalene sulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl ortributylphenyl polyglycol ether, alkyl aryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors and proteins, denatured proteins,polysaccharides (e.g., methylcellulose), hydrophobically modifiedstarches, polyvinyl alcohol, polycarboxylates, polyalkoxylates,polyvinyl amine, polyethyleneimine, polyvinylpyrrolidone and copolymersthereof.

Exemplary thickeners include, but are not limited to, polysaccharides,such as xanthan gum, and organic and inorganic sheet minerals, andmixtures thereof.

Exemplary antifoam agents include, but are not limited to, siliconeemulsions, long-chain alcohols, fatty acids, salts of fatty acids,organofluorine compounds, and mixtures thereof.

Exemplary antimicrobial agents include, but are not limited to,bactericides based on dichlorophen and benzyl alcohol hemiformal, andisothiazolinone derivatives, such as alkylisothiazolinones andbenzisothiazolinones, and mixtures thereof.

Exemplary antifreeze agents, include, but are not limited to ethyleneglycol, propylene glycol, urea, glycerol, and mixtures thereof.

Exemplary colorants include, but are not limited to, the dyes knownunder the names Rhodamine B, pigment blue 15:4, pigment blue 15:3,pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1,pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1,pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange34, pigment orange 5, pigment green 36, pigment green 7, pigment white6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acidred 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basicred 108, and mixtures thereof.

Exemplary adhesives include, but are not limited to,polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, andmixtures thereof.

In some embodiments, the additive includes a carrier. In someembodiments, the additive includes a liquid or solid carrier. In someembodiments, the additive includes an organic or inorganic carrier.Exemplary liquid carriers include, but are not limited to, petroleumfractions or hydrocarbons such as mineral oil, aromatic solvents,paraffinic oils, and the like or less, vegetable oils such as soybeanoil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconutoil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil,safflower oil, sesame oil, tung oil and the like or less, esters of theabove vegetable oils or less, esters of monoalcohols or dihydric,trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propyleneglycol dioleate, di-octyl succinate, di-butyl adipate, di-octylphthalate and the like or less, esters of mono, di and polycarboxylicacids and the like, toluene, xylene, petroleum naphtha, crop oil,acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene,perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propyleneglycol monomethyl ether and diethylene glycol monomethyl ether, methylalcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethyleneglycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone,N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and thelike, and water as well as mixtures thereof. Exemplary solid carriersinclude, but are not limited to, silicas, silica gels, silicates, talc,kaolin, limestone, lime, chalk, bole, loess, clay, dolomite,diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide,ground synthetic materials, pyrophyllite clay, attapulgus clay,kieselguhr, calcium carbonate, bentonite clay, Fuller's earth,cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnutshell flour, lignin, ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas, cereal meal, tree bark meal, wood meal and nutshellmeal, cellulose powders, and mixtures thereof.

In some embodiments, emulsions, pastes or oil dispersions, can beprepared by homogenizing (a) and (b) in water by means of wetting agent,tackifier, dispersant or emulsifier. In some embodiments, concentratessuitable for dilution with water are prepared, comprising (a), (b), awetting agent, a tackifier, and a dispersant or emulsifier.

In some embodiments, powders or materials for spreading and dusts can beprepared by mixing or concomitant grinding of (a) and (b) and optionallyan additional safener with a solid carrier.

In some embodiments, granules (e.g., coated granules, impregnatedgranules and homogeneous granules) can be prepared by binding the (a)and (b) to solid carriers.

The formulations disclosed herein can comprise a synergistic,herbicidally effective amount of (a) and (b). In some embodiments, theconcentrations of (a) and (b) in the formulations can be varied. In someembodiments, the formulations comprise from 1% to 95% (e.g., from 5% to95%, from 10% to 80%, from 20% to 70%, from 30% to 50%) by total weightof (a) and (b). In formulations designed to be employed as concentrates,(a) and (b) can be present in a concentration of from 0.1 to 98 weightpercent (0.5 to 90 weight percent), based on the total weight of theformulation. Concentrates can be diluted with an inert carrier, such aswater, prior to application. The diluted formulations applied toundesired vegetation or the locus of undesired vegetation can containfrom 0.0006 to 8.0 weight percent of (a) and (b) (e.g., from 0.001 to5.0 weight percent), based on the total weight of the dilutedformulation.

In some embodiments, (a) and (b), independently, can be employed in apurity of from 90% to 100% (e.g., from 95% to 100%) according to nuclearmagnetic resonance (NMR) spectrometry. In some embodiments, theconcentrations of (a), (b), and additional pesticides in theformulations can be varied. In some embodiments, the formulationscomprise from 1% to 95% (e.g., from 5% to 95%, from 10% to 80%, from 20%to 70%, from 30% to 50%) by total weight of (a), (b), and additionalpesticides. In some embodiments, (a), (b), and additional pesticides,independently, can be employed in a purity of from 90% to 100% (e.g.,from 95% to 100%) according to NMR spectrometry.

III. METHODS OF USE

The compositions disclosed herein can be applied in any known techniquefor applying herbicides. Exemplary application techniques include, butare not limited to, spraying, atomizing, dusting, spreading, or directapplication into water (in-water). The method of application can varydepending on the intended purpose. In some embodiments, the method ofapplication can be chosen to ensure the finest possible distribution ofthe compositions disclosed herein.

In some embodiments, a method of controlling undesirable vegetationwhich comprises contacting the vegetation or the locus thereof with orapplying to the soil or water to prevent the emergence or growth ofvegetation any of the compositions is disclosed herein.

The compositions disclosed herein can be applied pre-emergence (beforethe emergence of undesirable vegetation) or post-emergence (i.e., duringand/or after emergence of the undesirable vegetation). In someembodiments, the composition is applied post-emergence to theundesirable vegetation. In some embodiments, the pyridine carboxylicacid herbicide and the azole carboxylate safener are appliedsimultaneously.

When the compositions are used in crops, the compositions can be appliedafter seeding and before or after the emergence of the crop plants. Insome embodiments, the compositions disclosed herein show good croptolerance even when the crop has already emerged and can be appliedduring or after the emergence of the crop plants. In some embodiments,when the compositions are used in crops, the compositions can be appliedbefore seeding of the crop plants.

In some embodiments, the compositions disclosed herein are applied tovegetation or an area adjacent the vegetation or applying to soil orwater to prevent the emergence or growth of vegetation by spraying(e.g., foliar spraying). In some embodiments, the spraying techniquesuse, for example, water as carrier and spray volume rates of from 2liters per hectare (L/ha) to 2000 L/ha (e.g., from 10-1000 L/ha or from50-500 L/ha). In some embodiments, the compositions disclosed herein areapplied by the low-volume or the ultra-low-volume method, wherein theapplication is in the form of micro granules. In some embodiments,wherein the compositions disclosed herein are less well tolerated bycertain crop plants, the compositions can be applied with the aid of thespray apparatus in such a way that they come into little contact, ifany, with the leaves of the sensitive crop plants while reaching theleaves of undesirable vegetation that grows underneath or on the baresoil (e.g., post-directed or lay-by). In some embodiments, thecompositions disclosed herein can be applied as dry formulations (e.g.,granules, WDGs, etc.) into water.

In some embodiments, wherein the undesirable vegetation is treatedpost-emergence, the compositions disclosed herein are applied by foliarapplication. In some embodiments, herbicidal activity is exhibited bythe compounds of the mixture when they are applied directly to the plantor to the locus of the plant at any stage of growth or before plantingor emergence. The effect observed can depend upon the type ofundesirable vegetation to be controlled, the stage of growth of theundesirable vegetation, the application parameters of dilution and spraydrop size, the particle size of solid components, the environmentalconditions at the time of use, the specific compound employed, thespecific adjuvants and carriers employed, the soil type, and the like,as well as the amount of chemical applied. In some embodiments, theseand other factors can be adjusted to promote non-selective or selectiveherbicidal action.

The compositions and methods disclosed herein can be used to controlundesired vegetation in a variety of crop and non-crop applications. Insome embodiments, the compositions and methods disclosed herein can beused for controlling undesired vegetation in crops. In some embodiments,the undesirable vegetation is controlled in a row crop. Exemplary cropsinclude, but are not limited to, wheat, corn/maize, barley, triticale,rye, teff, oats, cotton, soy, sorghum, rice, sugarcane and range land(e.g., pasture grasses). In some embodiments, the compositions andmethods disclosed herein can be used for controlling undesiredvegetation in wheat, corn/maize, barley, tame oats, rice, or acombination thereof. In certain embodiments, the compositions andmethods disclosed herein can be used for controlling undesiredvegetation in wheat (Triticum aestivum). In certain embodiments, thecompositions and methods disclosed herein can be used for controllingundesired vegetation in corn/maize (Zea mays, ZEAMX). In certainembodiments, the compositions and methods disclosed herein can be usedfor controlling undesired vegetation in barley (Hordeum vulgare). Incertain embodiments, the compositions and methods disclosed herein canbe used for controlling undesired vegetation in tame oats (Avena sp.,AVESS). In certain embodiments, the compositions and methods disclosedherein can be used for controlling undesired vegetation in rice (Oryzasativa, ORYSA).

The compositions and methods disclosed herein can be used forcontrolling undesired vegetation in non-crop areas. Exemplary non-cropareas include, but are not limited to, turfgrass, pastures, grasslands,rangelands, fallow land, rights-of-way, aquatic settings, tree and vine,wildlife management areas, or rangeland. In some embodiments, thecompositions and methods disclosed herein can be used in industrialvegetation management (IVM) or for utility, pipeline, roadside, andrailroad rights-of-way applications. In some embodiments, thecompositions and methods disclosed herein can also be used in forestry(e.g., for site preparation or for combating undesirable vegetation inplantation forests). In some embodiments, the compositions and methodsdisclosed herein can be used to control undesirable vegetation inconservation reserve program lands (CRP), trees, vines, grasslands, andgrasses grown for seeds. In some embodiments, the compositions andmethods disclosed herein can be used on lawns (e.g., residential,industrial, and institutional), golf courses, parks, cemeteries,athletic fields, and sod farms.

The compositions and methods disclosed herein can also be used in cropplants that are resistant to, for instance, herbicides, pathogens,and/or insects. In some embodiments, the compositions and methodsdisclosed herein can be used in crop plants that are resistant to one ormore herbicides because of genetic engineering or breeding. In someembodiments, the compositions and methods disclosed herein can be usedin crop plants that are resistant to one or more pathogens such as plantpathogenous fungi owing to genetic engineering or breeding. In someembodiments, the compositions and methods disclosed herein can be usedin crop plants that are resistant to attack by insects owing to geneticengineering or breeding. Exemplary resistant crops include, but are notlimited to, crops that are resistant to photosystem II inhibitors, orcrop plants that, owing to introduction of the gene for Bacillusthuringiensis (or Bt) toxin by genetic modification, are resistant toattack by certain insects. In some embodiments, the compositions andmethods described herein can be used in conjunction with glyphosate,glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins,aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors,imidazolinones, acetolactate synthase (ALS) inhibitors,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,protoporphyrinogen oxidase (PPO) inhibitors, triazines, and bromoxynilto control vegetation in crops tolerant to glyphosate, glufosinate,dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates,acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactatesynthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, triazines,bromoxynil, or combinations thereof. In some embodiments, theundesirable vegetation is controlled in glyphosate, glufosinate,dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates,acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactatesynthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, triazines, andbromoxynil tolerant crops possessing single, multiple or stacked traitsconferring tolerance to single or multiple chemistries and/or multiplemodes of action. In some embodiments, the undesirable vegetation can becontrolled in a crop that is ACCase-tolerant, ALS-tolerant, or acombination thereof. The combination of (a), (b), and a complementaryherbicide or salt or ester thereof can be used in combination withherbicides that are selective for the crop being treated and whichcomplement the spectrum of weeds controlled by these compounds at theapplication rate employed. In some embodiments, the compositionsdescribed herein and other complementary herbicides are applied at thesame time, either as a combination formulation or as a tank mix, or assequential applications.

The compositions and methods may be used in controlling undesirablevegetation in crops possessing agronomic stress tolerance (including butnot limited to drought, cold, heat, salt, water, nutrient, fertility,pH), pest tolerance (including but not limited to insects, fungi andpathogens), and crop improvement traits (including but not limited toyield; protein, carbohydrate, or oil content; protein, carbohydrate, oroil composition; plant stature and plant architecture).

In some embodiments, the compositions disclosed herein can be used forcontrolling undesirable vegetation including grasses, broadleaf weeds,sedge weeds, and combinations thereof. In some embodiments, thecompositions and methods disclosed herein can be used for controllingundesirable vegetation including, but not limited to, Polygonum speciessuch as wild buckwheat (Polygonum convolvulus), Amaranthus species suchas pigweed (Amaranthus retroflexus), Chenopodium species such as commonlambsquarters (Chenopodium album L.), Sida species such as prickly sida(Sida spinosa L.), Ambrosia species such as common ragweed (Ambrosiaartemisiifolia), Cyperus species such as nutsedge (Cyperus esculentus),Setaria species such as giant foxtail (Setaria faberi), Sorghum species,Acanthospermum species, Anthemis species, Atriplex species, Brassicaspecies, Cirsium species, Convolvulus species, Conyza species, such ashorseweed (Conyza canadensis), Cassia species, Commelina species, Daturaspecies, Euphorbia species, Geranium species, Galinsoga species, Ipomoeaspecies such as morning-glory, Lamium species, Malva species, Matricariaspecies, Prosopis species, Rumex species, Sisymbrium species, Solanumspecies, Trifolium species, Xanthium species, Veronica species, Violaspecies such as wild pansy (Viola tricolor), common chickweed (Stellariamedia), velvetleaf (Abutilon theophrasti), hemp sesbania (Sesbaniaexaltata Cory), Anoda cristata, Bidens pilosa, Brassica kaber,shepherd's purse (Capsella bursa-pastoris), cornflower (Centaurea cyanusor Cyanus segetum), hempnettle (Galeopsis tetrahit), cleavers (Galiumaparine), Helianthus annuus, Desmodium tortuosum, kochia (Kochiascoparia), Medicago arabica, Mercurialis annua, Myosotis arvensis,common poppy (Papaver rhoeas), Raphanus raphanistrum, Russian thistle(Salsola kali), wild mustard (Sinapis arvensis), Sonchus arvensis,Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major,Plantago lanceolata, bird's-eye speedwell (Veronica persica) andspeedwell.

In some embodiments, the undesirable vegetation includes velvetleaf(ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthus retroflexus),winter rape (BRSNW, Brassica napus), lambsquarters (CHEAL, Chenopodiumalbum), thistle (CIRAR, Cirsium arvense), nutsedge (CYPES, Cyperusesculentus), poinsettia (EPHHL, Euphorbia heterophylla), wild buckwheat(POLCO, Polygonum convolvulus), giant foxtail (SETFA, Setaria faberi),sorghum (SORVU, Sorghum bicolor), chickweed (STEME, Stellaria media),wild pansy (VIOTR, Viola tricolor), or a combination thereof.

The herbicidal compositions described herein can be used to controlherbicide resistant or tolerant weeds. The methods employing thecompositions described herein may also be employed to control herbicideresistant or tolerant weeds. Exemplary resistant or tolerant weedsinclude, but are not limited to, biotypes resistant or tolerant toacetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)inhibitors (e.g., imidazolinones, sulfonylureas,pyrimidinylthiobenzoates, triazolopyrimidines,sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g.,phenylcarbamates, pyridazinones, triazines, triazinones, uracils,amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetylCoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates,cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoicacids, phenoxycarboxylic acids, pyridine carboxylic acids, quinolinecarboxylic acids), auxin transport inhibitors (e.g., phthalamates,semicarbazones), photosystem I inhibitors (e.g., bipyridyliums),5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g.,glyphosate), glutamine synthetase inhibitors (e.g., glufosinate,bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoicacids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors(e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g.,acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acidand lipid synthesis inhibitors (e.g., phosphorodithioates,thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogenoxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides,oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidinediones,thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g.,clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors(e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones,pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors(e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulosebiosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac,triazolocarboxamides), herbicides with multiple modes-of-action such asquinclorac, and unclassified herbicides such as arylaminopropionicacids, difenzoquat, endothall, and organoarsenicals. Exemplary resistantor tolerant weeds include, but are not limited to, biotypes withresistance or tolerance to multiple herbicides, biotypes with resistanceor tolerance to multiple chemical classes, biotypes with resistance ortolerance to multiple herbicide modes-of-action, and biotypes withmultiple resistance or tolerance mechanisms (e.g., target siteresistance or metabolic resistance).

By way of non-limiting illustration, examples of certain embodiments ofthe present disclosure are given below. Parts and percentages are on aper weight basis unless otherwise indicated.

EXAMPLES Example 1 Herbicidal Activity and Effect on Crop Injury onWheat of Fenchlorazole-Ethyl in Combination with Compounds of Formula(I) in Greenhouse Trials Methodology—Evaluation of PostemergenceHerbicidal Safening in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Stocks solutions of the safenerswere prepared following the same procedure. Spray solutions of thesafeners and experimental compound mixtures were prepared by adding thestock solutions to the appropriate amount of dilution solution to form a12 mL spray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. All herbicideapplication (component a) rates are in g ae/ha and all safener(component b) rates are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

The safener fenchlorazole-ethyl was combined with compound 1, compound2, compound 3, compound 4, compound 5, and compound 6, and applied towheat (TRZAS), and the phytotoxicity of the herbicidal compositions wasmeasured. In addition, the efficacy of the herbicidal composition onvelvetleaf (ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthusretroflexus), winter rape (BRSNW, Brassica napus), lambsquarters (CHEAL,Chenopodium album), thistle (CIRAR, Cirsium arvense), nutsedge (CYPES,Cyperus esculentus), poinsettia (EPHHL, Euphorbia heterophylla), wildbuckwheat (POLCO, Polygonum convolvulus), giant foxtail (SETFA, Setariafaberi), sorghum (SORVU, Sorghum bicolor), chickweed (STEME, Stellariamedia), and wild pansy (VIOTR, Viola tricolor) was evaluated. Theresults are summarized in Tables 1-6.

TABLE 1 Effect (% visual injury) of compound 1 on wheat (TRZAS).Application rate (g/ha) compound 1 35 0 35 fenchlorazole-ethyl 0 35 35TRZAS Obs 39 0 10 Exp — — 39 Δ −29 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 99 0 100 Exp — — 99 Δ 1 EPHHL Obs 100  0 100 Exp — — 100 Δ 0POLCO Obs 99 0 100 Exp — — 99 Δ 2 ABUTH Obs 85 0 70 Exp — — 85 Δ −15CIRAR Obs 90 0 85 Exp — — 90 Δ −5 g/ha = grams per hectare TRZAS =Triticum aestivum (spring wheat) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) EPHHL = Euphorbiaheterophylla (poinsettia) POLCO = Polygonum convolvulus (wild buckwheat)ABUTH = Abutilon theophrasti (velvetleaf) CIRAR = Cirsium arvense(thistle)

TABLE 2 Effect (% visual injury) of compound 2 on wheat (TRZAS).Application rate (g/ha) compound 2 35 0 35 fenchlorazole-ethyl 0 35 35TRZAS Obs 15 0 0 Exp — — 15 Δ −15 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 100  0 100 Exp — — 100 Δ 0 CHEAL Obs 97 0 100 Exp — — 97 Δ 3CIRAR Obs 70 0 80 Exp — — 70 Δ 10 VIOTR Obs 40 0 70 Exp — — 40 Δ 30POLCO Obs 100  0 100 Exp — — 100 Δ 0 SORVU Obs 70 0 80 Exp — — 70 Δ 10STEME Obs 100  0 100 Exp — — 100 Δ 0 g/ha = grams per hectare TRZAS =Triticum aestivum (spring wheat) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album(lambsquarters) CIRAR = Cirsium arvense (thistle) VIOTR = Viola tricolor(wild pansy) POLCO = Polygonum convolvulus (wild buckwheat) SORVU =Sorghum bicolor (sorghum) STEME = Stellaria media (chickweed)

TABLE 3 Effect (% visual injury) of compound 3 on wheat (TRZAS).Application rate (g/ha) compound 3 35 0 35 fenchlorazole-ethyl 0 35 35TRZAS Obs 30 0 0 Exp — — 30 Δ −30 ABUTH Obs 50 0 50 Exp — — 50 Δ 0 AMAREObs 75 0 90 Exp — — 75 Δ 15 BRSNW Obs 30 0 30 Exp — — 30 Δ 0 CHEAL Obs85 0 97 Exp — — 85 Δ 12 EPHHL Obs 100  0 100 Exp — — 100 Δ 0 POLCO Obs97 0 100 Exp — — 97 Δ 3 g/ha = grams per hectare TRZAS = Triticumaestivum (spring wheat) ABUTH = Abutilon theophrasti (velvetleaf) AMARE= Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) EPHHL = Euphorbia heterophylla(poinsettia) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 4 Effect (% visual injury) of compound 4 on wheat (TRZAS).Application rate (g/ha) compound 4 35 0 35 fenchlorazole-ethyl 0 35 35TRZAS Obs 40 0 15 Exp — — 40 Δ −25 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 97 0 95 Exp — — 97 Δ −2 CHEAL Obs 97 0 97 Exp — — 97 Δ 0 CIRARObs 75 0 80 Exp — — 75 Δ 5 CYPES Obs  0 0 10 Exp — — 0 Δ 10 EPHHL Obs100  0 100 Exp — — 100 Δ 0 POLCO Obs 100  0 100 Exp — — 100 Δ 0 STEMEObs 93 0 100 Exp — — 93 Δ 7 g/ha = grams per hectare TRZAS = Triticumaestivum (spring wheat) AMARE = Amaranthus retroflexus (pigweed) BRSNW =Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)CIRAR = Cirsium arvense (thistle) CYPES = Cyperus esculentus (nutsedge)EPHHL = Euphorbia heterophylla (poinsettia) POLCO = Polygonumconvolvulus (wild buckwheat) STEME = Stellaria media (chickweed)

TABLE 5 Effect (% visual injury) of compound 5 on wheat (TRZAS).Application rate (g/ha) compound 5 35 0 35 fenchlorazole-ethyl 0 35 35TRZAS Obs 45 0 35 Exp — — 45 Δ −10 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3CHEAL Obs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 80 0 80 Exp — — 80 Δ 0STEME Obs 85 0 93 Exp — — 85 Δ 8 g/ha = grams per hectare TRZAS =Triticum aestivum (spring wheat) ABUTH = Abutilon theophrasti(velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassicanapus (winter rape) CHEAL = Chenopodium album (lambsquarters) CIRAR =Cirsium arvense (thistle) STEME = Stellaria media (chickweed)

TABLE 6 Effect (% visual injury) of compound 6 on wheat (TRZAS).Application rate (g/ha) compound 6 35 0 35 fenchlorazole-ethyl 0 35 35TRZAS Obs 35 0 15 Exp — — 35 Δ −20 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 75 0 75 Exp — — 75 Δ 0CHEAL Obs 100  0 100 Exp — — 100 Δ 0 POLCO Obs 97 0 100 Exp — — 97 Δ 3SETFA Obs 10 0 80 Exp — — 10 Δ 70 STEME Obs 97 0 100 Exp — — 97 Δ 3 g/ha= grams per hectare TRZAS = Triticum aestivum (spring wheat) ABUTH =Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album(lambsquarters) POLCO = Polygonum convolvulus (wild buckwheat) SETFA =Setaria faberi (giant foxtail) STEME = Stellaria media (chickweed)

Example 2 Herbicidal Activity and Effect on Crop Injury on Wheat ofIsoxadifen-Ethyl in Combination with Compounds of Formula (I) inGreenhouse Trials Methodology—Evaluation of Postemergence HerbicidalSafening in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Stocks solutions of the safenerswere prepared following the same procedure. Spray solutions of thesafeners and experimental compound mixtures were prepared by adding thestock solutions to the appropriate amount of dilution solution to form a12 mL spray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. All herbicideapplication (component a) rates are in g ae/ha and all safener(component b) rates are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

The safener isoxadifen-ethyl was combined with compound 1, compound 2,compound 3, compound 4, compound 5, and compound 6, and applied to wheat(TRZAS), and the phytotoxicity of the herbicidal compositions wasmeasured. In addition, the efficacy of the herbicidal composition onvelvetleaf (ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthusretroflexus), winter rape (BRSNW, Brassica napus), lambsquarters (CHEAL,Chenopodium album), thistle (CIRAR, Cirsium arvense), wild buckwheat(POLCO, Polygonum convolvulus), giant foxtail (SETFA, Setaria faberi),chickweed (STEME, Stellaria media), and wild pansy (VIOTR, Violatricolor) was evaluated. The results are summarized in Tables 7-12.

TABLE 7 Effect (% visual injury) of compound 1 on wheat (TRZAS).Application rate (g/ha) compound 1 35 0 35 isoxadifen-ethyl 0 35 35TRZAS Obs 39 0 0 Exp — — 39 Δ −39 ABUTH Obs 85 0 85 Exp — — 85 Δ 0 AMAREObs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 99 0 100 Exp — — 99 Δ 1 POLCOObs 99 0 100 Exp — — 99 Δ 2 VIOTR Obs 64 0 70 Exp — — 64 Δ 6 CHEAL Obs100  0 93 Exp — — 100 Δ −7 CIRAR Obs 90 0 85 Exp — — 90 Δ −5 g/ha =grams per hectare TRZAS = Triticum aestivum (spring wheat) ABUTH =Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) POLCO = Polygonumconvolvulus (wild buckwheat) VIOTR = Viola tricolor (wild pansy) CHEAL =Chenopodium album (lambsquarters) CIRAR = Cirsium arvense (thistle)

TABLE 8 Effect (% visual injury) of compound 2 on wheat (TRZAS).Application rate (g/ha) compound 2 35 0 35 isoxadifen-ethyl 0 35 35TRZAS Obs 15 0 0 Exp — — 15 Δ −15 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 100  0 100 Exp — — 100 Δ 0 CHEAL Obs 97 0 100 Exp — — 97 Δ 3CIRAR Obs 70 0 85 Exp — — 70 Δ 15 VIOTR Obs 40 0 60 Exp — — 40 Δ 20POLCO Obs 100  0 100 Exp — — 100 Δ 0 g/ha = grams per hectare TRZAS =Triticum aestivum (spring wheat) ABUTH = Abutilon theophrasti(velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassicanapus (winter rape) CHEAL = Chenopodium album (lambsquarters) CIRAR =Cirsium arvense (thistle) VIOTR = Viola tricolor (wild pansy) POLCO =Polygonum convolvulus (wild buckwheat)

TABLE 9 Effect (% visual injury) of compound 3 on wheat (TRZAS).Application rate (g/ha) compound 3 35 0 35 isoxadifen-ethyl 0 35 35TRZAS Obs 30 0 0 Exp — — 30 Δ −30 ABUTH Obs 50 0 50 Exp — — 50 Δ 0 AMAREObs 75 0 85 Exp — — 75 Δ 10 BRSNW Obs 30 0 60 Exp — — 30 Δ 30 CHEAL Obs85 0 97 Exp — — 85 Δ 12 CIRAR Obs 50 0 60 Exp — — 50 Δ 10 POLCO Obs 97 0100 Exp — — 97 Δ 3 g/ha = grams per hectare TRZAS = Triticum aestivum(spring wheat) ABUTH = Abutilon theophrasti (velvetleaf) AMARE =Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 10 Effect (% visual injury) of compound 4 on wheat (TRZAS).Application rate (g/ha) compound 4 35 0 35 isoxadifen-ethyl 0 35 35TRZAS Obs 40 0 10 Exp — — 40 Δ −30 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3CHEAL Obs 97 0 97 Exp — — 97 Δ 0 CIRAR Obs 75 0 93 Exp — — 75 Δ 18 VIOTRObs 60 0 60 Exp — — 60 Δ 0 STEME Obs 93 0 95 Exp — — 93 Δ 2 g/ha = gramsper hectare TRZAS = Triticum aestivum (spring wheat) ABUTH = Abutilontheophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW= Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)CIRAR = Cirsium arvense (thistle) VIOTR = Viola tricolor (wild pansy)STEME = Stellaria media (chickweed)

TABLE 11 Effect (% visual injury) of compound 5 on wheat (TRZAS).Application rate (g/ha) compound 5 35 0 35 isoxadifen-ethyl 0 35 35TRZAS Obs 45 0 15 Exp — — 45 Δ −30 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3CHEAL Obs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 80 0 85 Exp — — 80 Δ 5VIOTR Obs 40 0 70 Exp — — 40 Δ 30 STEME Obs 85 0 100 Exp — — 85 Δ 15g/ha = grams per hectare TRZAS = Triticum aestivum (spring wheat) ABUTH= Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album(lambsquarters) CIRAR = Cirsium arvense (thistle) VIOTR = Viola tricolor(wild pansy) STEME = Stellaria media (chickweed)

TABLE 12 Effect (% visual injury) of compound 6 on wheat (TRZAS).Application rate (g/ha) compound 6 35 0 35 isoxadifen-ethyl 0 35 35TRZAS Obs 35 0 0 Exp — — 35 Δ −35 ABUTH Obs 80 0 80 Exp — — 80 Δ 0 AMAREObs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 75 0 95 Exp — — 75 Δ 20 CHEALObs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 75 0 80 Exp — — 75 Δ 5 VIOTRObs 30 0 80 Exp — — 30 Δ 50 STEME Obs 97 0 100 Exp — — 97 Δ 3 POLCO Obs97 0 100 Exp — — 97 Δ 3 SETFA Obs 10 0 60 Exp — — 10 Δ 50 g/ha = gramsper hectare TRZAS = Triticum aestivum (spring wheat) ABUTH = Abutilontheophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW= Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)CIRAR = Cirsium arvense (thistle) VIOTR = Viola tricolor (wild pansy)STEME = Stellaria media (chickweed) POLCO = Polygonum convolvulus (wildbuckwheat) SETFA = Setaria faberi (giant foxtail)

Example 3 Herbicidal Activity and Effect on Crop Injury on Wheat ofMefenpyr-Diethyl in Combination with Compounds of Formula (I) inGreenhouse Trials Methodology—Evaluation of Postemergence HerbicidalSafening in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Stocks solutions of the safenerswere prepared following the same procedure. Spray solutions of thesafeners and experimental compound mixtures were prepared by adding thestock solutions to the appropriate amount of dilution solution to form a12 mL spray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. All herbicideapplication (component a) rates are in g ae/ha and all safener(component b) rates are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

The safener mefenpyr-diethyl was combined with compound 1, compound 2,compound 3, compound 4, compound 5, compound 6, and applied to wheat(TRZAS), and the phytotoxicity of the herbicidal compositions wasmeasured. In addition, the efficacy of the herbicidal composition onvelvetleaf (ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthusretroflexus), winter rape (BRSNW, Brassica napus), lambsquarters (CHEAL,Chenopodium album), thistle (CIRAR, Cirsium arvense), wild buckwheat(POLCO, Polygonum convolvulus), sorghum (SORVU, Sorghum bicolor),chickweed (STEME, Stellaria media), and wild pansy (VIOTR, Violatricolor) was evaluated. The results are summarized in Tables 13-18.

TABLE 13 Effect (% visual injury) of compound 1 on wheat (TRZAS).Application rate (g/ha) compound 1 35 0 35 mefenpyr-diethyl 0 35 35TRZAS Obs 39 0 0 Exp — — 39 Δ −39 ABUTH Obs 85 0 85 Exp — — 85 Δ 0 AMAREObs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 99 0 100 Exp — — 99 Δ 1 CHEALObs 100  0 100 Exp — — 100 Δ 0 STEME Obs 100  0 100 Exp — — 100 Δ 0POLCO Obs 99 0 100 Exp — — 99 Δ 2 g/ha = grams per hectare TRZAS =Triticum aestivum (spring wheat) ABUTH = Abutilon theophrasti(velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassicanapus (winter rape) CHEAL = Chenopodium album (lambsquarters) STEME =Stellaria media (chickweed) POLCO = Polygonum convolvulus (wildbuckwheat)

TABLE 14 Effect (% visual injury) of compound 2 on wheat (TRZAS).Application rate (g/ha) compound 2 35 0 35 mefenpyr-diethyl 0 35 35TRZAS Obs 15 0 0 Exp — — 15 Δ −15 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 100  0 100 Exp — — 100 Δ 0 CHEAL Obs 97 0 100 Exp — — 97 Δ 3CIRAR Obs 70 0 85 Exp — — 70 Δ 15 POLCO Obs 100  0 100 Exp — — 100 Δ 0g/ha = grams per hectare TRZAS = Triticum aestivum (spring wheat) AMARE= Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 15 Effect (% visual injury) of compound 3 on wheat (TRZAS).Application rate (g/ha) compound 3 35 0 35 mefenpyr-diethyl 0 35 35TRZAS Obs 30 0 10 Exp — — 30 Δ −20 ABUTH Obs 50 0 50 Exp — — 50 Δ 0AMARE Obs 75 0 95 Exp — — 75 Δ 20 BRSNW Obs 30 0 60 Exp — — 30 Δ 30CHEAL Obs 85 0 97 Exp — — 85 Δ 12 CIRAR Obs 50 0 50 Exp — — 50 Δ 0 POLCOObs 97 0 97 Exp — — 97 Δ 0 g/ha = grams per hectare TRZAS = Triticumaestivum (spring wheat) ABUTH = Abutilon theophrasti (velvetleaf) AMARE= Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 16 Effect (% visual injury) of compound 4 on wheat (TRZAS).Application rate (g/ha) compound 4 35 0 35 mefenpyr-diethyl 0 35 35TRZAS Obs 40 0 10 Exp — — 40 Δ −30 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 97 Exp — — 97 Δ 0CHEAL Obs 97 0 100 Exp — — 97 Δ 3 CIRAR Obs 75 0 85 Exp — — 75 Δ 10VIOTR Obs 60 0 70 Exp — — 60 Δ 10 POLCO Obs 100  0 100 Exp — — 100 Δ 0g/ha = grams per hectare TRZAS = Triticum aestivum (spring wheat) ABUTH= Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album(lambsquarters) CIRAR = Cirsium arvense (thistle) VIOTR = Viola tricolor(wild pansy) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 17 Effect (% visual injury) of compound 5 on wheat (TRZAS).Application rate (g/ha) compound 5 35 0 35 mefenpyr-diethyl 0 35 35TRZAS Obs 45 0 20 Exp — — 45 Δ −25 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3CHEAL Obs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 80 0 85 Exp — — 80 Δ 5SORVU Obs 60 0 80 Exp — — 60 Δ 20 STEME Obs 85 0 85 Exp — — 85 Δ 0 VIOTRObs 40 0 50 Exp — — 40 Δ 10 g/ha = grams per hectare TRZAS = Triticumaestivum (spring wheat) ABUTH = Abutilon theophrasti (velvetleaf) AMARE= Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) SORVU = Sorghum bicolor (sorghum) STEME = Stellaria media(chickweed) VIOTR = Viola tricolor (wild pansy)

TABLE 18 Effect (% visual injury) of compound 6 on wheat (TRZAS).Application rate (g/ha) compound 6 35 0 35 mefenpyr-diethyl 0 35 35TRZAS Obs 35 0 10 Exp — — 35 Δ −25 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 75 0 90 Exp — — 75 Δ 15CHEAL Obs 100  0 100 Exp — — 100 Δ 0 VIOTR Obs 30 0 40 Exp — — 30 Δ 10POLCO Obs 97 0 100 Exp — — 97 Δ 3 g/ha = grams per hectare TRZAS =Triticum aestivum (spring wheat) ABUTH = Abutilon theophrasti(velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassicanapus (winter rape) CHEAL = Chenopodium album (lambsquarters) VIOTR =Viola tricolor (wild pansy) POLCO = Polygonum convolvulus (wildbuckwheat)

Example 4 Herbicidal Activity and Effect on Crop Injury on Corn/Maize ofFenchlorazole-Ethyl in Combination with Compounds of Formula (I) inGreenhouse Trials Methodology—Evaluation of Postemergence HerbicidalSafening in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Stocks solutions of the safenerswere prepared following the same procedure. Spray solutions of thesafeners and experimental compound mixtures were prepared by adding thestock solutions to the appropriate amount of dilution solution to form a12 mL spray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. All herbicideapplication (component a) rates are in g ae/ha and all safener(component b) rates are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

The safener fenchlorazole-ethyl was combined with compound 1, compound2, compound 5, and compound 6, and applied to corn/maize (ZEAMX) and thephytotoxicity of the herbicidal compositions was measured. In addition,the efficacy of the herbicidal composition on velvetleaf (ABUTH,Abutilon theophrasti), pigweed (AMARE, Amaranthus retroflexus), winterrape (BRSNW, Brassica napus), lambsquarters (CHEAL, Chenopodium album),thistle (CIRAR, Cirsium arvense), nutsedge (CYPES, Cyperus esculentus),poinsettia (EPHHL, Euphorbia heterophylla), wild buckwheat (POLCO,Polygonum convolvulus), giant foxtail (SETFA, Setaria faberi), sorghum(SORVU, Sorghum bicolor), and chickweed (STEME, Stellaria media) wasevaluated. The results are summarized in Tables 19-22.

TABLE 19 Effect (% visual injury) of compound 1 on corn/maize (ZEAMX).Application rate (g/ha) compound 1 35 0 35 fenchlorazole-ethyl  0 35  35ZEAMX Obs 40 0 35 Exp — — 40 Δ −5 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 99 0 100 Exp — — 99 Δ 1 CHEAL Obs 100  0 93 Exp — — 100 Δ −7CIRAR Obs 90 0 85 Exp — — 90 Δ −5 EPHHL Obs 100  0 100 Exp — — 100 Δ 0POLCO Obs 99 0 100 Exp — — 99 Δ 2 STEME Obs 100  0 100 Exp — — 100 Δ 0g/ha = grams per hectare ZEAMX = Zea mays (corn/maize) AMARE =Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) EPHHL = Euphorbia heterophylla (poinsettia) POLCO = Polygonumconvolvulus (wild buckwheat) STEME = Stellaria media (chickweed)

TABLE 20 Effect (% visual injury) of compound 4 on corn/maize (ZEAMX).Application rate (g/ha) compound 4 35 0 35 fenchlorazole-ethyl  0 35  35ZEAMX Obs 35 0 25 Exp — — 35 Δ −10 ABUTH Obs 80 0 70 Exp — — 80 Δ −10AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 95 Exp — — 97 Δ −2CHEAL Obs 97 0 97 Exp — — 97 Δ 0 CIRAR Obs 75 0 80 Exp — — 75 Δ 5 CYPESObs  0 0 10 Exp — — 0 Δ 10 EPHHL Obs 100  0 100 Exp — — 100 Δ 0 POLCOObs 100  0 100 Exp — — 100 Δ 0 SORVU Obs 80 0 80 Exp — — 80 Δ 0 STEMEObs 93 0 100 Exp — — 93 Δ 7 g/ha = grams per hectare ZEAMX = Zea mays(corn/maize) ABUTH = Abutilon theophrasti (velvetleaf) AMARE =Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbiaheterophylla (poinsettia) POLCO = Polygonum convolvulus (wild buckwheat)SORVU = Sorghum bicolor (sorghum) STEME = Stellaria media (chickweed)

TABLE 21 Effect (% visual injury) of compound 5 on corn/maize (ZEAMX).Application rate (g/ha) compound 5 35 0 35 fenchlorazole-ethyl  0 35  35ZEAMX Obs 35 0 20 Exp — — 35 Δ −15 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3CHEAL Obs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 80 0 80 Exp — — 80 Δ 0EPHHL Obs 100  0 100 Exp — — 100 Δ 0 POLCO Obs 100  0 100 Exp — — 100 Δ0 SORVU Obs 60 0 60 Exp — — 60 Δ 0 STEME Obs 85 0 93 Exp — — 85 Δ 8 g/ha= grams per hectare ZEAMX = Zea mays (corn/maize) ABUTH = Abutilontheophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW= Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)CIRAR = Cirsium arvense (thistle) EPHHL = Euphorbia heterophylla(poinsettia) POLCO = Polygonum convolvulus (wild buckwheat) SORVU =Sorghum bicolor (sorghum) STEME = Stellaria media (chickweed)

TABLE 22 Effect (% visual injury) of compound 6 on corn/maize (ZEAMX).Application rate (g/ha) compound 6 35 0 35 fenchlorazole-ethyl  0 35  35ZEAMX Obs 25 0 10 Exp — — 25 Δ −15 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 75 0 75 Exp — — 75 Δ 0CHEAL Obs 100  0 100 Exp — — 100 Δ 0 EPHHL Obs 100  0 100 Exp — — 100 Δ0 POLCO Obs 97 0 100 Exp — — 97 Δ 3 SETFA Obs 10 0 80 Exp — — 10 Δ 70SORVU Obs 70 0 70 Exp — — 70 Δ 0 STEME Obs 97 0 100 Exp — — 97 Δ 3 g/ha= grams per hectare ZEAMX = Zea mays (corn/maize) ABUTH = Abutilontheophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW= Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)EPHHL = Euphorbia heterophylla (poinsettia) POLCO = Polygonumconvolvulus (wild buckwheat) SETFA = Setaria faberi (giant foxtail)SORVU = Sorghum bicolor (sorghum) STEME = Stellaria media (chickweed)

Example 5 Herbicidal Activity and Effect on Crop Injury on Corn/Maize ofMefenpyr-Diethyl in Combination with Compounds of Formula (I) inGreenhouse Trials Methodology—Evaluation of Postemergence HerbicidalSafening in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Stocks solutions of the safenerswere prepared following the same procedure. Spray solutions of thesafeners and experimental compound mixtures were prepared by adding thestock solutions to the appropriate amount of dilution solution to form a12 mL spray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. All herbicideapplication (component a) rates are in g ae/ha and all safener(component b) rates are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

The safener mefenpyr-diethyl was combined with compound 1, compound 2,and compound 5, and applied to corn/maize (ZEAMX) and the phytotoxicityof the herbicidal compositions were measured. In addition, the efficacyof the herbicidal composition on velvetleaf (ABUTH, Abutilontheophrasti), pigweed (AMARE, Amaranthus retroflexus), winter rape(BRSNW, Brassica napus), lambsquarters (CHEAL, Chenopodium album),thistle (CIRAR, Cirsium arvense), nutsedge (CYPES, Cyperus esculentus),poinsettia (EPHHL, Euphorbia heterophylla), wild buckwheat (POLCO,Polygonum convolvulus), sorghum (SORVU, Sorghum bicolor), chickweed(STEME, Stellaria media), and wild pansy (VIOTR, Viola tricolor) wasevaluated. The results are summarized in Tables 23-25.

TABLE 23 Effect (% visual injury) of compound 1 on corn/maize (ZEAMX).Application rate (g/ha) compound 1 35 0 35 mefenpyr-diethyl 0 35 35ZEAMX Obs 40 0 30 Exp — — 40 Δ −10 ABUTH Obs 85 0 85 Exp — — 85 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 99 0 100 Exp — — 99 Δ 1CHEAL Obs 100  0 100 Exp — — 100 Δ 0 EPHHL Obs 100  0 100 Exp — — 100 Δ0 POLCO Obs 99 0 100 Exp — — 99 Δ 2 STEME Obs 100  0 100 Exp — — 100 Δ 0g/ha = grams per hectare ZEAMX = Zea mays (corn/maize) ABUTH = Abutilontheophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW= Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)EPHHL = Euphorbia heterophylla (poinsettia) POLCO = Polygonumconvolvulus (wild buckwheat) STEME = Stellaria media (chickweed)

TABLE 24 Effect (% visual injury) of compound 2 on corn/maize (ZEAMX).Application rate (g/ha) compound 2 35 0 35 mefenpyr-diethyl 0 35 35ZEAMX Obs 35 0 15 Exp — — 35 Δ −20 ABUTH Obs 80 0 75 Exp — — 80 Δ −5AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 100  0 100 Exp — — 100 Δ0 CHEAL Obs 97 0 100 Exp — — 97 Δ 3 CIRAR Obs 70 0 85 Exp — — 70 Δ 15EPHHL Obs 100  0 100 Exp — — 100 Δ 0 POLCO Obs 100  0 100 Exp — — 100 Δ0 g/ha = grams per hectare ZEAMX = Zea mays (corn/maize) ABUTH =Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus(pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album(lambsquarters) CIRAR = Cirsium arvense (thistle) EPHHL = Euphorbiaheterophylla (poinsettia) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 25 Effect (% visual injury) of compound 5 on corn/maize (ZEAMX).Application rate (g/ha) compound 5 35 0 35 mefenpyr-diethyl 0 35 35ZEAMX Obs 35 0 25 Exp — — 35 Δ −10 ABUTH Obs 80 0 80 Exp — — 80 Δ 0AMARE Obs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3CHEAL Obs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 80 0 85 Exp — — 80 Δ 5CYPES Obs  0 0 0 Exp — — 0 Δ 0 EPHHL Obs 100  0 100 Exp — — 100 Δ 0POLCO Obs 100  0 100 Exp — — 100 Δ 0 SORVU Obs 60 0 80 Exp — — 60 Δ 20VIOTR Obs 40 0 50 Exp — — 40 Δ 10 g/ha = grams per hectare ZEAMX = Zeamays (corn/maize) ABUTH = Abutilon theophrasti (velvetleaf) AMARE =Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbiaheterophylla (poinsettia) POLCO = Polygonum convolvulus (wild buckwheat)SORVU = Sorghum bicolor (sorghum) VIOTR = Viola tricolor (wild pansy)

Example 6 Herbicidal Activity and Effect on Crop Injury on Corn/Maize ofIsoxadifen-Ethyl in Combination with Compounds of Formula (I) inGreenhouse Trials Methodology—Evaluation of Postemergence HerbicidalSafening in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Stocks solutions of the safenerswere prepared following the same procedure. Spray solutions of thesafeners and experimental compound mixtures were prepared by adding thestock solutions to the appropriate amount of dilution solution to form a12 mL spray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. All herbicideapplication (component a) rates are in g ae/ha and all safener(component b) rates are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

The safener isoxadifen-ethyl was combined with compound 1, compound 2,compound 4, compound 5, and compound 6, and applied to corn/maize(ZEAMX) and the phytotoxicity of the herbicidal compositions wasmeasured. In addition, the efficacy of the herbicidal composition onvelvetleaf (ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthusretroflexus), winter rape (BRSNW, Brassica napus), lambsquarters (CHEAL,Chenopodium album), thistle (CIRAR, Cirsium arvense), poinsettia (EPHHL,Euphorbia heterophylla), wild buckwheat (POLCO, Polygonum convolvulus),giant foxtail (SETFA, Setaria faberi), chickweed (STEME, Stellariamedia), and wild pansy (VIOTR, Viola tricolor) was evaluated. Theresults are summarized in Tables 26-30.

TABLE 26 Effect (% visual injury) of compound 1 on corn/maize (ZEAMX).Application rate (g/ha) compound 1 35 0 35 isoxadifen-ethyl 0 35 35ZEAMX Obs 40 0 0 Exp — — 40 Δ −40 ABUTH Obs 85 0 85 Exp — — 85 Δ 0 AMAREObs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 99 0 100 Exp — — 99 Δ 1 POLCOObs 99 0 100 Exp — — 99 Δ 2 STEME Obs 100  0 100 Exp — — 100 Δ 0 VIOTRObs 64 0 70 Exp — — 64 Δ 6 g/ha = grams per hectare ZEAMX = Zea mays(corn/maize) ABUTH = Abutilon theophrasti (velvetleaf) AMARE =Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)POLCO = Polygonum convolvulus (wild buckwheat) STEME = Stellaria media(chickweed) VIOTR = Viola tricolor (wild pansy)

TABLE 27 Effect (% visual injury) of compound 2 on corn/maize (ZEAMX).Application rate (g/ha) compound 2 35 0 35 isoxadifen-ethyl 0 35 35ZEAMX Obs 35 0 0 Exp — — 35 Δ −35 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 100  0 100 Exp — — 100 Δ 0 CHEAL Obs 97 0 100 Exp — — 97 Δ 3CIRAR Obs 70 0 85 Exp — — 70 Δ 15 EPHHL Obs 100  0 100 Exp — — 100 Δ 0POLCO Obs 100  0 100 Exp — — 100 Δ 0 STEME Obs 100  0 100 Exp — — 100 Δ0 VIOTR Obs 40 0 60 Exp — — 40 Δ 20 g/ha = grams per hectare ZEAMX = Zeamays (corn/maize) AMARE = Amaranthus retroflexus (pigweed) BRSNW =Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)CIRAR = Cirsium arvense (thistle) EPHHL = Euphorbia heterophylla(poinsettia) POLCO = Polygonum convolvulus (wild buckwheat) STEME =Stellaria media (chickweed) VIOTR = Viola tricolor (wild pansy)

TABLE 28 Effect (% visual injury) of compound 4 on corn/maize (ZEAMX).Application rate (g/ha) compound 4 35 0 35 isoxadifen-ethyl 0 35 35ZEAMX Obs 35 0 0 Exp — — 35 Δ −35 ABUTH Obs 80 0 80 Exp — — 80 Δ 0 AMAREObs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3 CHEALObs 97 0 97 Exp — — 97 Δ 0 CIRAR Obs 75 0 93 Exp — — 75 Δ 18 STEME Obs93 0 95 Exp — — 93 Δ 2 g/ha = grams per hectare ZEAMX = Zea mays(corn/maize) ABUTH = Abutilon theophrasti (velvetleaf) AMARE =Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape)CHEAL = Chenopodium album (lambsquarters) CIRAR = Cirsium arvense(thistle) STEME = Stellaria media (chickweed)

TABLE 29 Effect (% visual injury) of compound 5 on corn/maize (ZEAMX).Application rate (g/ha) compound 5 35 0 35 isoxadifen-ethyl 0 35 35ZEAMX Obs 35 0 0 Exp — — 35 Δ −35 ABUTH Obs 80 0 80 Exp — — 80 Δ 0 AMAREObs 100  0 100 Exp — — 100 Δ 0 BRSNW Obs 97 0 100 Exp — — 97 Δ 3 CHEALObs 100  0 100 Exp — — 100 Δ 0 CIRAR Obs 80 0 85 Exp — — 80 Δ 5 STEMEObs 85 0 100 Exp — — 85 Δ 15 VIOTR Obs 40 0 70 Exp — — 40 Δ 30 g/ha =grams per hectare ZEAMX = Zea mays (corn/maize) ABUTH = Abutilontheophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNW= Brassica napus (winter rape) CHEAL = Chenopodium album (lambsquarters)CIRAR = Cirsium arvense (thistle) STEME = Stellaria media (chickweed)VIOTR = Viola tricolor (wild pansy)

TABLE 30 Effect (% visual injury) of compound 6 on corn/maize (ZEAMX).Application rate (g/ha) compound 6 35 0 35 isoxadifen-ethyl 0 35 35ZEAMX Obs 25 0 0 Exp — — 25 Δ −25 AMARE Obs 100  0 100 Exp — — 100 Δ 0BRSNW Obs 75 0 95 Exp — — 75 Δ 20 CHEAL Obs 100  0 100 Exp — — 100 Δ 0CIRAR Obs 75 0 80 Exp — — 75 Δ 5 STEME Obs 97 0 100 Exp — — 97 Δ 3 VIOTRObs 30 0 80 Exp — — 30 Δ 50 POLCO Obs 97 0 100 Exp — — 97 Δ 3 SETFA Obs10 0 60 Exp — — 10 Δ 50 g/ha = grams per hectare ZEAMX = Zea mays(corn/maize) AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassicanapus (winter rape) CHEAL = Chenopodium album (lambsquarters) CIRAR =Cirsium arvense (thistle) STEME = Stellaria media (chickweed) VIOTR =Viola tricolor (wild pansy) POLCO = Polygonum convolvulus (wildbuckwheat) SETFA = Setaria faberi (giant foxtail)

The compositions and methods of the appended claims are not limited inscope by the specific compositions and methods described herein, whichare intended as illustrations of a few aspects of the claims and anycompositions and methods that are functionally equivalent are intendedto fall within the scope of the claims. Various modifications of thecompositions and methods in addition to those shown and described hereinare intended to fall within the scope of the appended claims. Further,while only certain representative compositions and method stepsdisclosed herein are specifically described, other combinations of thecompositions and method steps also are intended to fall within the scopeof the appended claims, even if not specifically recited. Thus, acombination of steps, elements, components, or constituents may beexplicitly mentioned herein or less, however, other combinations ofsteps, elements, components, and constituents are included, even thoughnot explicitly stated. The term “comprising” and variations thereof asused herein is used synonymously with the term “including” andvariations thereof and are open, non-limiting terms. Although the terms“comprising” and “including” have been used herein to describe variousembodiments, the terms “consisting essentially of” and “consisting of”can be used in place of “comprising” and “including” to provide for morespecific embodiments of the invention and are also disclosed. Other thanin the examples, or where otherwise noted, all numbers expressingquantities of ingredients, reaction conditions, and so forth used in thespecification and claims are to be understood at the very least, and notas an attempt to limit the application of the doctrine of equivalents tothe scope of the claims, to be construed in light of the number ofsignificant digits and ordinary rounding approaches.

1. A safened herbicidal composition, comprising: (a) a pyridinecarboxylic acid herbicide defined by Formula (I)

wherein X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio; R¹ is OR^(1″) or NR^(1″)R^(1″), wherein R^(1′) ishydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) areindependently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring; A is one of groupsA1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN; R⁶, R^(6′), and R^(6″), if applicable to theA group, are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂; R⁷ and R^(7′) are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₁-C₄ haloalkylamino, or phenyl; R⁸ is hydrogen, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆trialkylsilyl, or phenyl; or an agriculturally acceptable N-oxide orsalt thereof; and (b) an azole carboxylate safener, or an agriculturallyacceptable salt or ester thereof.
 2. The composition of claim 1, whereinthe pyridine carboxylic acid herbicide comprises a compound defined byFormula (II)

wherein R¹ is OR^(1′) or NR^(1″)R^(1″), wherein R^(1′) is hydrogen,C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) areindependently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3,A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18,A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32,A33, A34, A35, or A36; R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN; R⁶, R^(6′), and R^(6″) are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂; R⁷ and R^(7′)are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl,cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl;and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl; or an agriculturallyacceptable N-oxide or salt thereof.
 3. The composition of claim 2,wherein R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, orC₇-C₁₀ arylalkyl; R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl,C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, or C₁-C₄ haloalkylthio; R³ and R⁴ arehydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino; A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15,A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32; R⁵ is hydrogen,halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl,C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino; R⁶,R^(6′), and R^(6″)are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl,amino or C₁-C₄ alkylamino; and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, or C₁-C₆alkylcarbamyl.
 4. The composition of claim 1, wherein the pyridinecarboxylic acid herbicide comprises a compound defined by Formula (III):

wherein X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio; R¹ is OR^(1′) or NR^(1″)R^(1″) wherein R^(1′) ishydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) areindependently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring; R⁶ and R^(6′) areindependently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl,cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN,or NO₂; R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl,C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, orphenyl; or an agriculturally acceptable N-oxide or salt thereof.
 5. Thecomposition of claim 1, wherein the pyridine carboxylic acid herbicidecomprises one of the following:


6. The composition of claim 1, wherein the pyridine carboxylic acidherbicide comprises


7. The composition of claim 1, wherein the azole carboxylate safener isselected from the group consisting of fenchlorazole, isoxadifen,mefenpyr, agriculturally acceptable salts or esters thereof, andcombinations thereof.
 8. The composition of claim 1, wherein the weightratio of (a) in g ae/ha to (b) in g ai/ha is from 65:1 to 1:5. 9.(canceled)
 10. (canceled)
 11. The composition of claim 1, furthercomprising an agriculturally acceptable adjuvant or carrier.
 12. Thecomposition of claim 1, further comprising an additional pesticide. 13.The composition of claim 1, wherein the active ingredients in thecomposition consist of (a) and (b).
 14. A method of controllingundesirable vegetation, comprising applying to vegetation or an areaadjacent the vegetation or applying to soil or water to control theemergence or growth of vegetation the composition of claim
 1. 15-20.(canceled)
 21. The method of claim 14, wherein (a) and (b) are appliedsimultaneously.
 22. The method of claim 14, wherein (a) and (b) areapplied post-emergence to the undesirable vegetation. 23-25. (canceled)26. The method of claim 14, wherein (a) is applied in amount of from 0.1g ae/ha to 300 g ae/ha.
 27. (canceled)
 28. The method of claim 14,wherein (b) is applied in amount of from 1 g ai/ha to 300 g ai/ha. 29.(canceled)
 30. (canceled)
 31. The method of claim 14, further comprisingapplying an additional pesticide.
 32. The method of claim 14, whereinthe undesirable vegetation is controlled in wheat, corn/maize, barley,triticale, rye, teff, oats, sorghum, rice, sugarcane, vineyards,orchards, perennial plantation crops, soybeans, cotton, sunflower,oilseed rape/canola, sugarbeets, turf, range and pasture, industrialvegetation management (IVM), rights-of-way, or combinations thereof. 33.The method of claim 14, wherein the undesirable vegetation is controlledin wheat, corn/maize, barley, tame oats, rice, or combinations thereof.34-37. (canceled)
 38. The method of claim 14, wherein the undesirablevegetation is controlled in a glyphosate-, glufosinate-, dicamba-,phenoxy auxin-, pyridyloxy auxin-, aryloxyphenoxypropionate-, acetyl CoAcarboxylase (ACCase) inhibitor-, imidazolinone-, acetolactate synthase(ALS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, triazine-, orbromoxynil-tolerant crop.
 39. (canceled)
 40. The method of claim 38,wherein the tolerant crop is wheat, corn/maize, barley, tame oats, rice,or combinations thereof. 41-44. (canceled)
 45. The method of claim 14,wherein the undesirable vegetation includes a broadleaf weed.
 46. Themethod of claim 14, wherein the undesirable vegetation comprises aherbicide resistant or tolerant weed.
 47. (canceled)
 48. (canceled) 49.The method of claim 14, wherein the undesirable vegetation includesvelvetleaf (ABUTH, Abutilon theophrasti), pigweed (AMARE, Amaranthusretroflexus), winter rape (BRSNW, Brassica napus), lambsquarters (CHEAL,Chenopodium album), thistle (CIRAR, Cirsium arvense), nutsedge (CYPES,Cyperus esculentus), poinsettia (EPHHL, Euphorbia heterophylla), wildbuckwheat (POLCO, Polygonum convolvulus), giant foxtail (SETFA, Setariafaberi), sorghum (SORVU, Sorghum bicolor), chickweed (STEME, Stellariamedia), wild pansy (VIOTR, Viola tricolor), or a combination thereof.50. The method of claim 14, wherein the active ingredients applied tothe vegetation or an area adjacent the vegetation or applied to soil orwater to control the emergence or growth of vegetation consist of (a)and (b).